AN ASYMMETRIC-SYNTHESIS OF THE FULLY FUNCTIONALIZED AB RING-SYSTEM OF 12-DEMETHYLTAXOL VIA SUCCESSIVE STEREOSELECTIVE ALLYLATION AND INTRAMOLECULAR ALDOL REACTIONS
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-pmethoxybenzyloxy-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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Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
Iwadare, H
Sakoh, H
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Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
Sakoh, H
Arai, H
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Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
Arai, H
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Shiina, I
Mukaiyama, T
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Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan