Volume 31, Issue 16
Natural Products
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ChemInform Abstract: An Effective Method for the Preparation of Optically Active Polyoxy 8-Membered Ring Enone Corresponding to the B Ring of Taxol.

Isamu Shiina

Isamu Shiina

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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Jun Shibata

Jun Shibata

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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Yumiko Imai

Yumiko Imai

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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Ryoutarou Ibuka

Ryoutarou Ibuka

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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Hidehiko Fujisawa

Hidehiko Fujisawa

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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Iwao Hachiya

Iwao Hachiya

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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Teruaki Mukaiyama

Teruaki Mukaiyama

Dep. Appl. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku, Tokyo 162, Japan

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First published: 09 June 2010

Abstract

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ChemInform Abstract

An effective method for the preparation of 8-membered ring enone (XI), a key intermediate in taxol synthesis, starting from D-pantolactone (I) is accomplished. Key steps of the reaction sequence are the diastereoselective hydroxylation of olefin (IV), the diastereoselective aldol reaction of trialkoxyaldehyde (VI) with ketene acetal (VII) and the aldol-type cyclization of oxoaldehyde (IX).

chemical structure image

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