Volume 29, Issue 31
Natural Products
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ChemInform Abstract: A β-Lactone-Based Strategy Applied to the Total Synthesis of (8S,21S,22S,23R)- and (8R,21S,22S,23R)-Okinonellin B.

W. D. SCHMITZ

W. D. SCHMITZ

Dep. Chem., Tex. A&M Univ., College Station, TX 77843, USA

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N. B. MESSERSCHMIDT

N. B. MESSERSCHMIDT

Dep. Chem., Tex. A&M Univ., College Station, TX 77843, USA

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D. ROMO

D. ROMO

Dep. Chem., Tex. A&M Univ., College Station, TX 77843, USA

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First published: 20 June 2010

Abstract

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ChemInform Abstract

The key steps in the synthesis of the title compounds (X) are tandem Mukaiyama aldol—lactonization of the aldehyde (IV) and tandem debenzylation—transacylation of the β-lactone (VI). Natural okinonellin B presumably possesses (8R,21R,22R,23S) stereochemistry.

chemical structure image

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