A new route to seven- and eight-membered carbocycles

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5233-5236

  U, Jong Sun ^a   Lee, Jinhwa ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; NATURAL PRODUCT;

ARTICLE; CYCLIZATION; OXIDATION; PARTIAL DRUG SYNTHESIS; TECHNIQUE;

EID: 0030859015     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01142-8     Document Type: Article

References (28)

1. For general reviews, see: (a) Rigby, J. H. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: New York, 1988; Vol. 1, pp 545-576.
2. (b) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
3. For the notable examples of other direct annulation processes, see: (a) Trost, B. M.; Vos, B. A.; Brzezowski, C. M.; Martina, D. P. Tetrahedron Lett. 1992, 33, 717.
4. (b) Kim, S.-J.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073 and references cited therein.
5. (a) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079.
6. (b) Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849.
7. (a) Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291.
8. (b) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
9. (c) Lee, J.; Cha, J. K. J. Org. Chem. 1997, 62, 1584.
10. We recently reported an alternate method for a seven-membered ring annulation by the sequential application of the Kulinkovich hydroxycyclopropanation and subsequent oxy-Cope rearrangement: Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.
11. (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244.
12. (b) Kulinkovich, O. G.; Savchenko, A. I.; Sviridov, S. V.; Vasilevskii, D. A. Mendeleev Commun. 1993, 192 and references cited therein. See also:
13. (c) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
14. (d) de Meijere, A.; Kozhushkov, S. I.; Spaeth, T.; Zefirov, N. S. J. Org. Chem. 1993, 58, 502.
15. (e) Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413.
16. (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073.
17. (b) Ito, Y.; Fujii, S.; Nakatsuka, M.; Kawamoto, F.; Saegusa, T. Org. Synth. Coll. Vol. VI 1988, 327.
18. 3 for a one-step preparation of enones: Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819 and refereces cited therein.
19. The requisite cyclization substrates 7a,b, 10, 13, 16, 19, and 22 were prepared by standard methods and details will be reported in a full paper.
20. (a) Unoptimized yield.
21. (b) As 19 was prepared as a 2:1 mixture of cis-and trans-ring junction diastereomers, the bicyclic enone 21 was isolated as a 2:1 diastereomeric mixture, and each isomer was separated and fully characterized.
22. (c) We believe that the actual yield for the oxidation-dehydrochlorination sequence is somewhat higher, since these cyclopropanols, in particular strained tricyclic compounds, are found to undergo decomposition in storage.
23. (a) Available in large quantities from Cayman Chemical, Ann Arbor, MI 48108.
24. 9
25. A new method for ring opening of the aminocyclopropanes has recently been developed in our laboratory: Lee, J.; U, J. S.; Cha, J. K. unpublished results.
26. Cf. For previous successful syntheses, see: (a) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735.
27. (b) Boeckman, R. K., Jr.; Arvanitis, A.; Voss, M. E. J. Am. Chem. Soc. 1989, 111, 2737.
28. We are grateful to the National Institutes of Health (GM 35956) for generous financial support and a Research Career Development Award (GM00575 to J.K.C.).