Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran

Chemical Communications

Volumn , Issue 21, 2002, Pages 2542-2543

  Tanabe, Yoo ^a   Mitarai, Kumi ^a   Higashi, Takahiro ^a   Misaki, Tomonori ^a   Nishii, Yoshinori ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FURANONE DERIVATIVE; KETONE; LACTONE DERIVATIVE; MENTHOFURAN; PERFUME;

ADDITION REACTION; ALDOL REACTION; ARTICLE; POLYMERIZATION; SYNTHESIS;

EID: 0036977478     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b208077j     Document Type: Article

References (34)

1. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
2. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
3. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
4. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
5. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
6. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
7. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
8. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
9. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
10. For books and a review: (a) P. G. Marshal, in Rodd's Chemistry of Carbon Compounds, Elsevier, New York, 2nd. edn., 1970, vol. 2, Part D, p. 369; (b) Y. S. Rao, Chem. Rev., 1976, 76, 625; (c) D. W. Knight, Contemporary Organic Synthesis, 1994, 1, 287; for recent papers (d) G. J. Hollingworth, G. Perkins and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 1913; (e) G. J. Hollingworth, A. M. E. Richecoeur and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1996, 2833; (f) M. Ohno, Y. Yamamoto and S. Eguchi, Synlett, 1998, 1167; (g) A. M. E. Richecoeur and J. B. Sweeney, Tetrahedron Lett., 1998, 39, 8901; (h) P. Forgione, P. D. Wilson and A. G. Fallis, Tetrahedron Lett., 2000, 41, 17; (i) P. C. Montevecchi and M. L. Navacchia, Tetrahedron, 2000, 56, 9339; (j) Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett., 2001, 42, 6789.
11. Y. Tanabe and N. Ohno, J. Org. Chem., 1988, 53, 1560.
12. (a) Y. Yoshida, R. Hayashi, H. Sumihara and Y. Tanabe, Tetrahedron Lett., 1997, 38, 8727;
13. (b) Y. Yoshida, N. Matsumoto, R. Hamasaki and Y. Tanabe, Tetrahedron Lett., 1999, 40, 4227;
14. (c) Y. Tanabe, N. Matsumoto, S. Funakoshi and N. Manta, Synlett, 2001, 1959;
15. (d) Y. Tanabe, N. Matsumoto, T. Higashi, T. Misaki, T. Itoh, M. Yamamoto, K. Mitarai and Y. Nishii, Tetrahedron, 2002, 58, 8269. Related powerful Ti (Zr)-Claisen condensation processes
16. (e) Y. Tanabe, R. Hamasaki and S. Funakoshi, Chem. Commun., 2001, 1674;
17. (f) Y. Tanabe, A. Makita, S. Funakoshi, R. Hamasaki and T. Kawakusu, Adv. Synth. Catal., 2002, 344, 507.
18. (a) I. Sakata and T. Hashizume, Agric. Biol. Chem., 1973, 37, 2441;
19. (b) K. Takahashi, T. Someya, S. Muraki and T. Yoshida, Agric. Biol. Chem., 1980, 44, 1535.
20. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
21. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
22. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
23. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
24. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
25. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
26. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
27. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
28. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
29. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
30. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
31. Synthesis of racemic form: (a) S. Tuboi, K. Shimozuka and A. Takeda, J. Org. Chem., 1980, 45, 1517; (b) R. M. Cory, B. M. Ritchie and A. M. Shirer, Tetrahedron Lett., 1990, 31, 6789; (c) S. P. Chavan, P. K. Zubaidha and N. R. Ayyangar, Tetrahedron Lett., 1992, 33, 4605; (d) C. Tanyeli, Z. Caliskan and A. S. Demir, Synth. Commun., 1997, 27, 3471Synthesis of R-form (e) K. Shishido, O. Irie and M. Shibuya, Tetrahedron Lett., 1992, 33, 4589; (f) M. Carda and J. A. Marco, Tetrahedron, 1992, 48, 9789; (g) S. P. Chavan, P. K. Zubaidha and V. D. Dhondge, Tetrahedron, 1993, 49, 6429; (h) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831; (i) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37; (j) M. Shimizu, T. Kamikubo and K. Ogasawara, Synlett, 1998, 655; (k) H. M. C. Ferraz, M. V. A. Grazini, C. M. R. Riberio, U. Brocksom and T. J. Brocksom, J. Org. Chem., 2000, 65, 2606; (l) J.-M. Gaudin, Tetrahedron, 2000, 56, 4769.
32. (a) K. Shishido, T. Takata, K. Utimoto and M. Shibuya, Heterocycles, 1992, 33, 73;
33. (b) A. Padwa, M. Ishida, C. L. Mullera and S. S. Murphee, J. Org. Chem., 1992, 57, 1710;
34. K. Shishido, K. Utimoto, T. Takata and M. Shibuya, Heterocycles, 1993, 36, 345.