Stereoselective synthesis of tetrahydropyran and oxepane systems by the endo-cyclization of hydroxy styrylepoxides

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5545-5548

  Matsukura, Hiroko ^a   Morimoto, Masamichi ^a   Koshino, Hiroyuki ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; OXEPANE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0030747943     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01197-0     Document Type: Article

References (22)

1. Visiting scientist from Tanabe Seiyaku Co., Ltd.
2. Lin, Y. Y.; Risk, M.; Ray, M. S.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773.
3. (a) For a review of the synthesis of trans-fused polycyclic ethers, see: Alvarex, E.; Candenas, M.-L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953, and references cited therein.
4. (b) Nakata, T.; Nomura, S.; Matsukura, H. Tetrahedron Lett. 1996, 37, 213.
5. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123, 127.
6. Baldwin, J. E. J. Chem. Soc. Chem. Comm. 1976, 734.
7. (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K.; Somers, P. K. J. Chem. Soc. Chem. Commun. 1985, 1359.
8. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
9. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5335.
10. Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927.
11. (e) Suzuki, T.; Sato, O.; Hirama, M. Tetrahedron Lett. 1990, 31, 4747.
12. (f) Mukai, C.; Ikeda, Y.; Sugimoto, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2179.
13. (g) Mukai, C.; Sugimoto, Y.; Ikeda, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2183.
14. (h) Janda, K. D.; Shevlin, C. G.; Lerner, R. A. J. Am. Chem. Soc. 1995, 117, 2659.
15. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158.
16. Matsukura, H.; Morimoto, M.; Nakata, T. Chemistry Lett. 1996, 487.
17. 2.
18. 3P=CHPh and desilylation with TBAF produced (Z)-styryl-trans-epoxide 4, a 9:1 mixture of (Z)- and (E)-cis-8a,b, (Z)-trans-10 and (Z)-cis-11, respectively. (equation presented)
19. The stereostructures of 5, 6, 9, 12, and 13 were confirmed by their NMR (NOE and/or HMBC) analyses.
20. The temperature below 0 °C did not complete the cyclization.
21. Reactions of the corresponding vinyl trans-epoxides under the same conditions effected the 6- and 7-exo-cyclizations to give the tetrahydropyran and oxepane, respectively, which were, however, isolated in low yield after column chromatography.
22. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett., 1996, 37, 6365.