Chemoenzymatic Synthesis of All Four Stereoisomers of Sphingosine from Chlorobenzene: Glycosphingolipid Precursors

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 510-520

  Nugent, Thomas C ^a,b   Hudlicky, Tomas ^a  

^a University of Florida ^*  (United States)

^b University of Arizona ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001318436     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971335a     Document Type: Article

References (110)

1. Preliminary results of this work have been published; see: (a) Hudlicky, T.; Nugent, T. C.; Griffith, W. J. Org. Chem. 1994, 59, 7944. (b) Banwell, M. G.; Haddad, N.; Hudlicky, T.; Nugent, T. C.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans., 1 1997, 1779.
2. Preliminary results of this work have been published; see: (a) Hudlicky, T.; Nugent, T. C.; Griffith, W. J. Org. Chem. 1994, 59, 7944. (b) Banwell, M. G.; Haddad, N.; Hudlicky, T.; Nugent, T. C.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans., 1 1997, 1779.
3. Hakomori, S. Sphingolipid Biochemistry. In Handbook of Lipid Research; Kanfer, J. N., Hakomori, S., Eds.; Plenum: New York, 1983; Vol. 3, p 1.
4. (a) Polt, R.; Peterson, M. A. J. Org. Chem. 1993, 58, 4309 and references cited therein,
5. (b) Merrill, A. H. Curr. Topics Membr. 1994, 40, 361.
6. (c) Chaban, V.; Mason, W.; Bunting, R.; Baranska, J. Mol. Biol. Cell 1995, 6, 2229.
7. (d) Choi, O. H.; Kim, J. H.; Kinet, J. P. Nature 1996, 380, 634.
8. (e) Cuvillier, O.; Pirianov, G.; Kleuser, B.; Vanek, P. G.; Coso, O. A.; Gutkind, J. S.; Spiegel, S. Nature 1996, 381, 800.
9. (f) Inooka, S.; Toyokuni, T. Biochem. Biophys. Res. Commun. 1996, 218, 872
10. (a) Nicolaou, K. C. Chemtracts-Org. Chem. 1991, 4, 181.
11. (b) Schmidt, R. R. Pure Appl. Chem. 1989, 61, 1257.
12. Harouse, J. M.; Bhat, S.; Spitalnik, S. L.; Laughlin, M.; Stefano, K.; Silberberg, D. H.; Gonzalez-Scarano, F. Science 1991, 253, 320.
13. Hannun, Y. A.; Bell, R. M. Science 1989, 243, 500.
14. Merrill, A. H.; Nimkar, S.; Menaldino, D.; Hannun, Y. A.; Loomis, C.; Bell, R. M.; Tyagi, S. R.; Lambeth, J. D.; Stevens, V. L.; Hunter, R.; Liotta, D. C. Biochemistry 1989, 28, 3138.
15. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
16. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
17. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
18. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
19. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
20. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
21. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
22. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
23. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
24. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
25. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
26. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
27. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
28. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
29. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
30. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
31. Syntheses of sphingosine from carbohydrates: (a) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 4127. (b) Obayashi, M.; Schlosser, M. Chem. Lett. 1985, 1715. (c) Schmidt, R. R.; Zimmermann, P. Angew. Chem., Int. Ed. Engl. 1986, 25, 725. (d) Schmidt, R. R.; Zimmermann, P. Tetrahedron Lett. 1986, 27, 481. (e) Kiso, M.; Nakamura, A.; Tomita, Y.; Hasegawa, A. Carbohydr. Res. 1986, 158, 101. (f) Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. J. Carbohydr. Chem. 1986, 5 (2), 335. (g) Koike, K.; Numata, M.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Carbohydr. Chem. 1986, 158, 113. (h) Zimmermann, P.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 663. (i) Sugawara, T.; Norisada, M. Carbohydr. Res. 1989, 194, 125. (j) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191. (k) Murakami, T.; Minamikawa, H.; Hato, M. Tetrahedron Lett. 1994, 35, 745. (1) Schmidt, R. R.; Wild, B. Tetrahedron: Asymmetry 1994, 5, 2195. (m) Li, Y. L.; Sun, X. L.; Wu, Y. L. Tetrahedron 1994, 50, 10727. (n) Schmidt, R. R.; Bär, T.; Wild, B. Synthesis 1995, 869. (o) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823. (p) Shinozaki, K.; Mizuno, K.; Masaki, Y. Chem. Pharm. Bull. 1996, 44, 927. (q) Synthesis from D-isoascorbic acid: Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J. C. Tetrahedron: Asymmetry 1996, 7, 897.
32. Syntheses of sphingosine from L-serine: (a) Newman, H. J. Am. Chem. Soc. 1973, 95, 4098. (b) Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393. (c) Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320. (d) Herold, P. Helv. Chim. Acta 1988, 71, 354. (e) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037. (f) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395. (g) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439. (h) Polt, R.; Peterson, M. A.; DeYoung, L. J. Org. Chem. 1992, 57, 5469.
33. Syntheses of sphingosine from L-serine: (a) Newman, H. J. Am. Chem. Soc. 1973, 95, 4098. (b) Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393. (c) Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320. (d) Herold, P. Helv. Chim. Acta 1988, 71, 354. (e) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037. (f) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395. (g) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439. (h) Polt, R.; Peterson, M. A.; DeYoung, L. J. Org. Chem. 1992, 57, 5469.
34. Syntheses of sphingosine from L-serine: (a) Newman, H. J. Am. Chem. Soc. 1973, 95, 4098. (b) Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393. (c) Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320. (d) Herold, P. Helv. Chim. Acta 1988, 71, 354. (e) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037. (f) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395. (g) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439. (h) Polt, R.; Peterson, M. A.; DeYoung, L. J. Org. Chem. 1992, 57, 5469.
35. Syntheses of sphingosine from L-serine: (a) Newman, H. J. Am. Chem. Soc. 1973, 95, 4098. (b) Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393. (c) Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320. (d) Herold, P. Helv. Chim. Acta 1988, 71, 354. (e) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037. (f) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395. (g) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439. (h) Polt, R.; Peterson, M. A.; DeYoung, L. J. Org. Chem. 1992, 57, 5469.
36. Syntheses of sphingosine from L-serine: (a) Newman, H. J. Am. Chem. Soc. 1973, 95, 4098. (b) Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393. (c) Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320. (d) Herold, P. Helv. Chim. Acta 1988, 71, 354. (e) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037. (f) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395. (g) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439. (h) Polt, R.; Peterson, M. A.; DeYoung, L. J. Org. Chem. 1992, 57, 5469.
37. Syntheses of sphingosine from L-serine: (a) Newman, H. J. Am. Chem. Soc. 1973, 95, 4098. (b) Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393. (c) Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320. (d) Herold, P. Helv. Chim. Acta 1988, 71, 354. (e) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037. (f) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395. (g) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439. (h) Polt, R.; Peterson, M. A.; DeYoung, L. J. Org. Chem. 1992, 57, 5469.
38. Syntheses of sphingosine from L-serine: (a) Newman, H. J. Am. Chem. Soc. 1973, 95, 4098. (b) Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393. (c) Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320. (d) Herold, P. Helv. Chim. Acta 1988, 71, 354. (e) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037. (f) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395. (g) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439. (h) Polt, R.; Peterson, M. A.; DeYoung, L. J. Org. Chem. 1992, 57, 5469.
39. Syntheses of sphingosine from L-serine: (a) Newman, H. J. Am. Chem. Soc. 1973, 95, 4098. (b) Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393. (c) Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320. (d) Herold, P. Helv. Chim. Acta 1988, 71, 354. (e) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037. (f) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395. (g) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439. (h) Polt, R.; Peterson, M. A.; DeYoung, L. J. Org. Chem. 1992, 57, 5469.
40. 9aOnce this reference point has been established, comparison of the Fischer projections of D-erythrose and sphingosine clearly shows their analogous spatial arrangement. This fact alone determines whether two vicinal chiral centers are described as erythro or threo, not their stereochemical R or S assignment; i.e., D-erythrose has the 2S, 3R configuration, and D-erythro-sphingosine (1a) has the 2S,3R configuration, but it is irrelevant. When sphingosine 1b is depicted in a Fischer projection, it resembles L-threose and not D-threose. Chemical equation presented.
41. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
42. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
43. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
44. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
45. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
46. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
47. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
48. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
49. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
50. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
51. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
52. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
53. Miscellaneous approaches to sphingosines: (a) Shapiro, D.; Segal, K. H. J. Am. Chem. Soc. 1954, 76, 5894. (b) Shapirio, D.; Segal, K. H.; Flowers, H. M. J. Am. Chem. Soc. 1958, 80, 1194. (c) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491. (d) Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1985, 69, 368. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917. (f) Findeis, M. A.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2838. (g) Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910. (h) Shibuya, H.; Kawashima, K.; Ikeda, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 7205. (i) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 820. (j) Somfai, P.; Olsson, R. Tetrahedron 1993, 49, 6645. (k) Solladié-Cavallo, A.; Koessler, J. L. J. Org. Chem. 1994, 59, 3240. (1) Enders, D.; Whitehouse, D. L.; Runsink, J. Chem. Eur. J. 1995, 1, 382. (m) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349 and references cited therein.
54. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
55. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
56. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
57. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
58. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
59. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
60. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
61. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
62. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
63. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
64. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
65. For recent examples of arenediols in synthesis, see: (a) Hudlicky, T.; Seoane, G.; Pettus, T. J. Org. Chem. 1989, 54, 4239. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683. (c) Downing, W.; Latouche, R.; Pitoll, C. A.; Pryce, R. J.; Roberts, S. M.; Ryback, G.; Williams, J. O. J. Chem. Soc., Perkin Trans. 1 1990, 2613. (d) Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741. (e) Boyd, D. R.; Dority, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666. (f) Carless, H. A. J. Tetrahedron Lett. 1992, 6379. (g) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1. (h) Hudlicky, T.; Mandel, M.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331. (i) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985. (j) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099. (k) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (l) Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry 1997, 8, 975.
66. For comprehensive reviews of cyclohexadiene-cis-diol chemistry, see: (a) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Jansen Chim. Acta 1990, 8, 3. (b) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (c) Brown, S. M.;
67. For comprehensive reviews of cyclohexadiene-cis-diol chemistry, see: (a) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Jansen Chim. Acta 1990, 8, 3. (b) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (c) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, p 271. (e) Grund, A. D. SIM NEWS 1995, 45, 59. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; Chapter 14.
68. For comprehensive reviews of cyclohexadiene-cis-diol chemistry, see: (a) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Jansen Chim. Acta 1990, 8, 3. (b) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (c) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, p 271. (e) Grund, A. D. SIM NEWS 1995, 45, 59. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; Chapter 14.
69. For comprehensive reviews of cyclohexadiene-cis-diol chemistry, see: (a) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Jansen Chim. Acta 1990, 8, 3. (b) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (c) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, p 271. (e) Grund, A. D. SIM NEWS 1995, 45, 59. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; Chapter 14.
70. For comprehensive reviews of cyclohexadiene-cis-diol chemistry, see: (a) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Jansen Chim. Acta 1990, 8, 3. (b) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (c) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, p 271. (e) Grund, A. D. SIM NEWS 1995, 45, 59. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; Chapter 14.
71. For comprehensive reviews of cyclohexadiene-cis-diol chemistry, see: (a) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Jansen Chim. Acta 1990, 8, 3. (b) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (c) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, p 271. (e) Grund, A. D. SIM NEWS 1995, 45, 59. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; Chapter 14.
72. For comprehensive reviews of cyclohexadiene-cis-diol chemistry, see: (a) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Jansen Chim. Acta 1990, 8, 3. (b) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (c) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, p 271. (e) Grund, A. D. SIM NEWS 1995, 45, 59. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; Chapter 14.
73. For comprehensive reviews of cyclohexadiene-cis-diol chemistry, see: (a) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Jansen Chim. Acta 1990, 8, 3. (b) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (c) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, p 271. (e) Grund, A. D. SIM NEWS 1995, 45, 59. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; Chapter 14.
74. For comprehensive reviews of cyclohexadiene-cis-diol chemistry, see: (a) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Jansen Chim. Acta 1990, 8, 3. (b) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (c) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Practice; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, p 271. (e) Grund, A. D. SIM NEWS 1995, 45, 59. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; Chapter 14.
75. (a) Commercially available from Genencor International, Inc., Palo Alto, CA.
76. (b) Gibson, D. T.; Kock, J. R.; Kallio, R. E. Biochemistry 1968, 7, 2653.
77. (c) Gibson, D. T.; Koch, J. R.; Schuld, C. L.; Kallio, R. E. Biochemistry 1968, 7, 3795.
78. (d) Gibson, D. T.; Hensley, M.; Yoshioka, H.; Mabry, J. J. Biochemistry 1970, 9, 1626.
79. (e) Gibson, D. T. Crit. Rev. Microbiol. 1971, 1, 199.
80. (f) Gibson, D. T. Tox. Environ. Chem. 1982, 5, 237.
81. (g) Gibson, D. T.; Subramanian, V. In Microbial Degradation of Organic Compounds; Gibson, D. T., Ed.; Microbiology Series 13; Marcel Dekker: New York, 1984; Chapter 7.
82. (h) Gibson, D. T.; Zylstra, G. J.; Chauhan, S. In Pseudomonas: Biotransformations, Pathenogenesis and Evolving Biotechnology; Silver, S., Ed.; American Society for Microbiology: Washington, DC, 1990; Chapter 13, p 121.
83. (i) Zylstra, G. J.; Gibson, D. T. In Genetic Engineering; Setlow, J. A., Ed.; Pergamon: New York, 1991; Vol. 13, p 183.
84. (a) Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc. 1990, 112, 9439.
85. (b) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. Tetrahedron Lett. 1989, 30, 4053.
86. (c) Hudlicky, T.; Price, J. D. Synlett 1990, 159.
87. 3 (0.27 M), DMF, 12 h at 55°C, then 12 h at rt, 91% yield. (Note: The corresponding bromohydrin of 11 could not be synthesized without scrambling the stereochemistry at the allylic site, i.e., a 1:1 mixture of epimeric products was observed. T. Nugent and T. Hudlicky, unpublished results.) chemical equation presented.
88. J. Rouden and T. Hudlicky, unpublished results.
89. 4 (excess), MeOH, rt. Chemical equation presented.
90. 2 in MeOH (w/v), see: Szarek, W. A.; Zamojski, A.; Tiwari, K. N.; Ison, E. R. Tetrahedron Lett. 1986, 27, 3827. Unfortunately these neutral deprotection conditions were unknown to us when we were trying to synthesize 17b.
91. We believe that the lactols 19b and 20b are the products of reduction of the corresponding lactones - for precedent, see refs 12i.j.
92. 12b was subjected to our Wittig conditions. Chemical equation presented.
93. (a) Schlosser, M.; Tuong, H. B.; Schaub, B. Tetrahedron Lett. 1985, 26, 311.
94. (b) Bestmann, H. J.; Vostrowsky, O. In Topics in Current Chemistry; Boschke, F. L., Ed.; Springer-Verlag: New York, 1983; Vol. 109, p 106.
95. (a) Conia, J. M.; Limasset, J. C. Bull. Soc. Chem. Fr. 1967, 6, 1936.
96. (b) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103.
97. (c) Short, R. P.; Ranu, B. C.; Revol, J. M.; Hudlicky, T. J. Org. Chem. 1983, 48, 4453.
98. In our initial communication detailing the synthesis of D-erythro- and L-threo-sphingosine, we reported that a 400-W lamp was used; however, all photoisomerizations were carried out with a 450-W lamp.
99. 26
100. Moussebois, C.; Dale, J. J. Chem. Soc. C 1966, 260.
101. The sample was kindly provided by Professor Robin Polt of the University of Arizona. (Note: In the Experimental Section of the Polt paper, ref 9h, sphingosine 1b is referred to as the D-threo isomer; see ref 10 for further clarification.)
102. (a) Trippett, S. Chem. Soc. Rev. 1963, 17, 406.
103. For a more recent review on Wittig reactions, see: (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
104. (a) Pilard, S.; Vaultier, M. Tetrahedron Lett. 1984, 25, 1555.
105. (b) Falck, J. R.; Manna, S.; Viala, J.; Siddhanta, A. K; Moustakis, C. A.; Capdevila, J. Tetrahedron Lett. 1985, 26, 2287.
106. (c) Lin, T. C.; Cheng, M. C.; Peng, S. M.; Liu, S. T.; Kiang, F. M. J. Chin. Chem. Soc. 1995, 42, 543.
107. These products were not isolated until the synthesis of D-threo-sphingosine (1d). One possible reaction pathway for the formation of octacosene and sphingosine is shown below. Chemical equation presented.
108. 11h
109. Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. J. Org. Chem., 1993, 58, 832.
110. For the preparation of sodium amylate, see: Short, R. P.; Ranu, J. M.; Hudlicky, T. J. Org. Chem. 1983, 48, 4453. The solution of sodium amylate must be heated to 65°C and transferred quickly to the cooled solution of the phosphonium salt via syringe; otherwise, the amylate salt precipitates in the syringe.