Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Stereocontrolled Synthesis of the BC Ring System of Taxol
Isamu ShiinaHayato IwadareHiroki SakohYu-ichirou TaniMasatoshi HasegawaKatsuyuki SaitohTeruaki Mukaiyama
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1997 Volume 26 Issue 11 Pages 1139-1140

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Abstract

Optically active 2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(4-methoxybenzyloxy)–8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one 2 that corresponds to BC ring system of Taxol was prepared from 8-membered ring enone 3 in high yield via stereoselctive Michael addition and successive intramolecular aldol cyclization. The above 8-membered ring enone 3 was synthesized from the linear optically active polyoxy-compound 4 by SmI2-mediated intramolecular aldol cyclization.

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© 1997 The Chemical Society of Japan
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