Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
An Asymmetric Synthesis of the Fully Functionalized AB Ring System of 12-Demethyltaxol via Successive Stereoselective Allylation and Intramolecular Aldol Reactions
Isamu ShiinaHayato IwadareMasahiro SaitohNaoto OhkawaToshihiro NishimuraTeruaki Mukaiyama
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1995 Volume 24 Issue 9 Pages 781-782

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Abstract

Optically active 9-t-butyldiphenylsiloxy-11,11-dimethyl-5-methoxymethoxy-1,2,6-tribenzyloxybicyclo[5.3.1]undec-3,7-diene (12) was synthesized from diketone 9 via an intramolecular aldol reaction. The diketone 9 was synthesized from 7-t-butyldimethylsiloxy-4,8-dibenzyloxy-6,6-dimethyl-5-p-methoxy-benzyloxy-2-cycloocten-1-one (1) by way of a two-step sequence using diastereoselective allylation with allylmagnesium bromide followed by Wacker oxidation.

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© 1995 The Chemical Society of Japan
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