Practical synthesis of four stereoisomers of 6-(t-butyldiphenylsiloxy)- 3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol via dithiane coupling with oxirane

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 11, 1999, Pages 2501-2507

  Ide, Mitsuaki ^a   Tsunashima, Keiji ^a   Nakata, Masaya ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 (BUTYLDIPHENYLSILOXY) 3,5 DIMETHYL 1 (TRIPHENYLMETHOXY)HEXANE 2,4 DIOL; ETHYLENE OXIDE; UNCLASSIFIED DRUG;

ANION TRANSPORT; ARTICLE; CHIRALITY; COUPLING FACTOR; DERIVATIZATION; DRUG SYNTHESIS; EPOXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 0032719262     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.2501     Document Type: Article

References (23)

1. M. Ide and M. Nakata, Bull. Chem. Soc. Jpn., 72, 2491 (1999).
2. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc., 109, 5765 (1987).
3. a) Y. Kobayashi, Y. Kitano, Y. Takeda, and F. Sato, Tetrahedron, 42, 2937 (1986).
4. b) S. Hoagland, Y. Morita, D. L. Bai, H.-P. Märki, K. Kees, L. Brown, and C. H. Heathcock, J. Org. Chem., 53, 4730 (1988).
5. J. C. Shattuck and J. Meinwald, Tetrahedron Lett., 38, 8461 (1997).
6. a) J. A. Dale, D. L. Dull, and H. S. Mosher, J. Org. Chem., 34, 2543 (1969).
7. b) J. A. Dale and H. S. Mosher, J. Am. Chem. Soc., 95, 512 (1973).
8. a) J. D. White, P. Theramongkol, C. Kuroda, and J. R. Engebrecht, J. Org. Chem., 53, 5909 (1988).
9. b) S. T. Pickard, H. E. Smith, P. L. Polavarapu, T. M. Black, A. Rauk, and D. Yang, J. Am. Chem. Soc., 114, 6850 (1992).
10. J. D. White, T.-S. Kim, and M. Nambu, J Am. Chem. Soc., 119, 103 (1997).
11. a) E. Fujita, Y. Nagao, and K. Kaneko, Chem. Pharm. Bull., 26, 374.3 (1978).
12. b) R. Bernardi and D. Ghiringhelli, J. Org. Chem., 52, 5021 (1987).
13. S. Kiyooka, H. Kuroda, and Y. Shimasaki, Tetrahedron Lett., 27, 3009 (1986).
14. D. A. Evans, K. T. Chapman, and E. M. Carreira, J. Am. Chem. Soc., 110, 3560 (1988).
15. a) S. D. Rychnovsky and D. J. Skalitzky, Tetrahedron Lett., 31, 945 (1990).
16. b) S. D. Rychnovsky, B. Rogers, and G. Yang, J. Org. Chem., 58, 3511 (1993).
17. S. D. Rychnovsky, G. Yang, and J. P. Powers, J. Org. Chem., 58, 5251 (1993).
18. S. D. Rychnovsky, B. N. Rogers, and T. I. Richardson, Acc. Chem. Res., 31, 9 (1998).
19. D. A. Evans, D. L. Rieger, and J. R. Gage, Tetrahedron Lett., 31, 7099 (1990).
20. a) H. Kosugi, H. Konta, and H. Uda, J. Chem. Soc., Chem. Commun., 1985, 211.
21. b) G. Solladié, C. Fréchou, G. Demailly, and C. Greek, J. Org. Chem., 51, 1912 (1986).
22. K. Narasaka and F.-C. Pai, Tetrahedron, 40, 2233 (1984).
23. T. Oishi and T. Nakata, Acc. Chem. Res., 17, 338 (1984).