Stereoselective construction of eight-membered carbocycles by brook rearrangement-mediated [3 + 4] annulation

Organic Letters

Volumn 4, Issue 6, 2002, Pages 1031-1033

  Takeda, Kei ^a,b   Sawada, Yuji ^a   Sumi, Koichi ^b  

^a HIROSHIMA UNIV SCHOOL OF MEDICINE   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

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ARTICLE;

EID: 0042366249     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0256318     Document Type: Article

References (21)

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11. For a recent example of the synthesis of eight-membered carbocycles using the temporary bridge concept, see: (a) Rodriguez, J. R.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2000, 2, 3209-3212.
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14. This compound was prepared by House's method for cyclooctenone. House, H. O.; Sieloff, R. F.; Lee, T. V.; DeTar, M. B. J. Org. Chem. 1980, 45, 1800-1806.
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17. (a) Vishwakarma, L. C.; Stringer, O. D.; Davis, F. A.; Pribish, J.; Vedejs, E. Org. Synth. 1987, 66, 203-210.
18. (b) Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241-3243. The 3-nitrophenyl derivative was used to obtain better chromatographic separation after the reaction. The reaction using the parent phenyl derivative resulted in the formation of inseparable mixtures.
19. The use of KHMDS. the more common base for Davis' hydroxylation, was less efficient. The addition of HMPA also resulted in lower yields.
20. Di Grandi, M. J.; Cobum, C. A.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 7728-7731.
21. For transformation of the y-silyl enol silyl ether moiety in 10a,b into the corresponding α,β-enone by NBS/TBAF, see: ref 2d. Also, it is well-known that a dimethylphenylsilyl group can act as a hydroxyl surrogate in combination with Fleming's oxidative desilylation protocol; see: Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1, 1995, 317-337.