Unexpected rearrangement during biomimetic entry toward a taxane skeleton

Bicyclo[9.3.1]pentadecatriene derivative 4 which corresponds to a precursor of taxol in a biomimetic entry was constructed by means of TiCl 4Zn promoted McMurry cyclization and Mitsunobu inversion. Treatment of 4 with mercuric triflate afforded an unexpected rearrangement-transannular cyclization p...

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Bibliographic Details
Published in:Tetrahedron letters 1998-01, Vol.39 (5), p.389-392
Main Authors: Nishizawa, Mugio, Imagawa, Hiroshi, Hyodo, Ikumi, Takeji, Miho, Morikuni, Eiko, Asoh, Kohsuke, Yamada, Hidetoshi
Format: Article
Language:English
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Summary:Bicyclo[9.3.1]pentadecatriene derivative 4 which corresponds to a precursor of taxol in a biomimetic entry was constructed by means of TiCl 4Zn promoted McMurry cyclization and Mitsunobu inversion. Treatment of 4 with mercuric triflate afforded an unexpected rearrangement-transannular cyclization product 5. Bicyclo[9,3,1]pentadecatriene derivative, corresponds to a precursor of taxol in a biomimetic route, afforded unexpected rearrangement-transannular cyclization product by the treatment with mercuric triflate in the presence of TMU.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10556-1