Enantiospecific synthesis of a differentially protected L-chiro-inositol from D-xylose

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6497-6500

  Kornienko, Alexander ^a   D'Alarcao, Marc ^a  

^a TUFTS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INOSITOL; XYLOSE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030817673     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01513-X     Document Type: Article

References (38)

1. Mato, J.M.; Kelly, K.L.; Alber, A.; Jarett, L.; Corkey, B.E.; Cashel, J.A.; Zopf, D. Biochem. Biophys. Res. Commun. 1987, 146, 764-770. Larner, J.; Huang, L.C.; Schwartz, C.F.W.; Oswald, A.S.; Shen, T.Y.; Kinter, M.; Tang, G.; Zeller, K. ibid. 1988, 151, 1416-1426.
2. Mato, J.M.; Kelly, K.L.; Alber, A.; Jarett, L.; Corkey, B.E.; Cashel, J.A.; Zopf, D. Biochem. Biophys. Res. Commun. 1987, 146, 764-770. Larner, J.; Huang, L.C.; Schwartz, C.F.W.; Oswald, A.S.; Shen, T.Y.; Kinter, M.; Tang, G.; Zeller, K. ibid. 1988, 151, 1416-1426.
3. (a) Tagliaferri, F.; Wang, S.N.; Berlin, W.K.; Outten, R.A.; Shen, T.Y. Tetrahedron Lett. 1990, 31, 1105-1108.
4. (b) Jaramillo, C.; Martin-Lomas, M. ibid. 1991, 32, 2501-2504.
5. (c) Reddy, K.K.; Falck, J.R.; Capdevila, J. ibid. 1993, 34, 7869-7872.
6. (d) Jaramillo, C.; Chiara, J.L.; Martin-Lomas, M. J. Org. Chem. 1994, 59, 3135-3141.
7. (e) Chiara, J.L.; Valle, N. Tetrahedron Asymmetry 1995, 6, 1895-1898.
8. (f) Hudlicky, T.; Price, J.D.; Rulin, F.; Tsunoda, T. J. Amer. Chem. Soc. 1990, 112, 9439-9440.
9. (g) Mandel, M.; Hudlicky, T.; Kwart, L.D.; Whited, G.M. J. Org. Chem. 1993, 58, 2331-2333.
10. (h) Mandel, M.; Hudlicky, T. J. Chem. Soc. Perkin Trans. 1 1993, 741-743.
11. (i) Hudlicky, T.; Thorpe, A.J. Synlett 1994, 899-901.
12. Modest amounts of D-chiro-inositol can be obtained by demethylation of (+)-pinitol found in the extracts of sugar pine (Pinas lambertiana Dougl) wood dust: Anderson, A.B. Ind. Eng. Chem. 1953, 593-596. It is also accessible by ether cleavage of the natural antibiotic kasugamycin: Umezawa, H.; Okami, Y.; Hashimoto, T.; Suhara, Y.; Hamada, M.; Takeuchi, T. J. Antibiot. (Tokyo) Ser. A 1965, 18, 101-103. For a synthesis of D-chiro-inositol using a biocatalytic approach see: ref. 2g.
13. Modest amounts of D-chiro-inositol can be obtained by demethylation of (+)-pinitol found in the extracts of sugar pine (Pinas lambertiana Dougl) wood dust: Anderson, A.B. Ind. Eng. Chem. 1953, 593-596. It is also accessible by ether cleavage of the natural antibiotic kasugamycin: Umezawa, H.; Okami, Y.; Hashimoto, T.; Suhara, Y.; Hamada, M.; Takeuchi, T. J. Antibiot. (Tokyo) Ser. A 1965, 18, 101-103. For a synthesis of D-chiro-inositol using a biocatalytic approach see: ref. 2g.
14. Plourde, R.; d'Alarcao, M. Tetrahedron Lett. 1990, 31, 2693-2696. Plourde, R.; d'Alarcao, M.; Saltiel, A.R. J. Org. Chem. 1992, 57, 2606-2610.
15. Plourde, R.; d'Alarcao, M. Tetrahedron Lett. 1990, 31, 2693-2696. Plourde, R.; d'Alarcao, M.; Saltiel, A.R. J. Org. Chem. 1992, 57, 2606-2610.
16. It is understood that the enantiomeric derivatized D-chiro-inositol could be prepared in a similar manner from inexpensive L-xylose.
17. Tejima, S.; Ness, R.K.; Kaufman, R.L.; Fletcher, H.G. Carbohydr. Res. 1968, 7, 485-490. Tsuda, Y.; Nunozawa, T.; Yoshimoto, K. Chem. Pharm. Bull. 1980, 28, 3223-3231.
18. Tejima, S.; Ness, R.K.; Kaufman, R.L.; Fletcher, H.G. Carbohydr. Res. 1968, 7, 485-490. Tsuda, Y.; Nunozawa, T.; Yoshimoto, K. Chem. Pharm. Bull. 1980, 28, 3223-3231.
19. For other examples of methylenation of an anomeric position see: Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Gazzetta Chimica Italiana, 1984, 114, 193-195. Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Carbohydr. Res. 1984, 131, 180-184. Lancelin, J.-M.; Pougny, J.-R.; Sinay, P. ibid. 1985, 136, 369-374. Nicotra, F.; Panza, L.; Ronchetti, F.; Russo, G.; Toma, L. ibid. 1987, 171, 49-57.
20. For other examples of methylenation of an anomeric position see: Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Gazzetta Chimica Italiana, 1984, 114, 193-195. Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Carbohydr. Res. 1984, 131, 180-184. Lancelin, J.-M.; Pougny, J.-R.; Sinay, P. ibid. 1985, 136, 369-374. Nicotra, F.; Panza, L.; Ronchetti, F.; Russo, G.; Toma, L. ibid. 1987, 171, 49-57.
21. For other examples of methylenation of an anomeric position see: Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Gazzetta Chimica Italiana, 1984, 114, 193-195. Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Carbohydr. Res. 1984, 131, 180-184. Lancelin, J.-M.; Pougny, J.-R.; Sinay, P. ibid. 1985, 136, 369-374. Nicotra, F.; Panza, L.; Ronchetti, F.; Russo, G.; Toma, L. ibid. 1987, 171, 49-57.
22. For other examples of methylenation of an anomeric position see: Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Gazzetta Chimica Italiana, 1984, 114, 193-195. Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Carbohydr. Res. 1984, 131, 180-184. Lancelin, J.-M.; Pougny, J.-R.; Sinay, P. ibid. 1985, 136, 369-374. Nicotra, F.; Panza, L.; Ronchetti, F.; Russo, G.; Toma, L. ibid. 1987, 171, 49-57.
23. Mancuso, A.J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
24. 2 in a chelation controlled Grignard addition see: Keck, G.E.; Andrus, M.B.; Romer, D.R. J. Org. Chem. 1991, 56, 417-420.
25. Alcohols 4a and 4b were not completely separable by column chromatography. Mixtures enriched in either 4a or 4b were used in this experiment.
26. Corey, E.J.; Venkateswarlu, A. J. Amer. Chem. Soc. 1972, 94, 6190-6191.
27. 2 pinacol coupling in the synthesis of cyclitols see: Chiara, J.L.; Martin-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972. Guidot, J.P.; Gall, T.L.; Mioskowski, C. ibid. 1994, 35, 6671-6672. Sawada, T.; Shirai, R.; Iwasaki, S. ibid. 1996, 37, 885-886. Carpintero, M.; Fernandez-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916-1917. See also ref. 2e.
28. 2 pinacol coupling in the synthesis of cyclitols see: Chiara, J.L.; Martin-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972. Guidot, J.P.; Gall, T.L.; Mioskowski, C. ibid. 1994, 35, 6671-6672. Sawada, T.; Shirai, R.; Iwasaki, S. ibid. 1996, 37, 885-886. Carpintero, M.; Fernandez-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916-1917. See also ref. 2e.
29. 2 pinacol coupling in the synthesis of cyclitols see: Chiara, J.L.; Martin-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972. Guidot, J.P.; Gall, T.L.; Mioskowski, C. ibid. 1994, 35, 6671-6672. Sawada, T.; Shirai, R.; Iwasaki, S. ibid. 1996, 37, 885-886. Carpintero, M.; Fernandez-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916-1917. See also ref. 2e.
30. 2 pinacol coupling in the synthesis of cyclitols see: Chiara, J.L.; Martin-Lomas, M. Tetrahedron Lett. 1994, 35, 2969-2972. Guidot, J.P.; Gall, T.L.; Mioskowski, C. ibid. 1994, 35, 6671-6672. Sawada, T.; Shirai, R.; Iwasaki, S. ibid. 1996, 37, 885-886. Carpintero, M.; Fernandez-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916-1917. See also ref. 2e.
31. Chiara, J.L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125-1128.
32. 6Si: C, 70.18; H, 7.85. Found: C, 70.21; H, 7.95.
33. 3): δ 5.34 (dd, 9.8; 3.4 Hz, H5), 5.17 (dd, 4.3; 3.4 Hz, H6), 3.98 (dd, 4.3; 2.8 Hz, H1), 3.95 (ψt, 9.8 Hz, H3), 3.80 (ψt, 9.8 Hz, H4), 3.63 (dd, 9.8; 2.8 Hz, H2).
34. 1H NMR spectra of 10 obtained from the two different sources were indistinguishable.
35. For some other strategies see: Watanabe, Y.; Mitani, M.; Ozaki, S. Chemistry Lett. 1987, 123-126. Sato, K.; Sakuma, S.; Muramatsu, S.; Bokura, M. ibid. 1991, 1473-1474. Bender, S.L.; Budhu, R. J. Amer. Chem. Soc. 1991, 113, 9883-9885. Sato, K.; Bokura, M.; Taniguchi, M. Bull. Chem. Soc. Jpn. 1994, 67, 1633-1640. See also ref. 12, 2b,d.
36. For some other strategies see: Watanabe, Y.; Mitani, M.; Ozaki, S. Chemistry Lett. 1987, 123-126. Sato, K.; Sakuma, S.; Muramatsu, S.; Bokura, M. ibid. 1991, 1473-1474. Bender, S.L.; Budhu, R. J. Amer. Chem. Soc. 1991, 113, 9883-9885. Sato, K.; Bokura, M.; Taniguchi, M. Bull. Chem. Soc. Jpn. 1994, 67, 1633-1640. See also ref. 12, 2b,d.
37. For some other strategies see: Watanabe, Y.; Mitani, M.; Ozaki, S. Chemistry Lett. 1987, 123-126. Sato, K.; Sakuma, S.; Muramatsu, S.; Bokura, M. ibid. 1991, 1473-1474. Bender, S.L.; Budhu, R. J. Amer. Chem. Soc. 1991, 113, 9883-9885. Sato, K.; Bokura, M.; Taniguchi, M. Bull. Chem. Soc. Jpn. 1994, 67, 1633-1640. See also ref. 12, 2b,d.
38. For some other strategies see: Watanabe, Y.; Mitani, M.; Ozaki, S. Chemistry Lett. 1987, 123-126. Sato, K.; Sakuma, S.; Muramatsu, S.; Bokura, M. ibid. 1991, 1473-1474. Bender, S.L.; Budhu, R. J. Amer. Chem. Soc. 1991, 113, 9883-9885. Sato, K.; Bokura, M.; Taniguchi, M. Bull. Chem. Soc. Jpn. 1994, 67, 1633-1640. See also ref. 12, 2b,d.