Volume 31, Issue 34
Natural Products
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ChemInform Abstract: Total Synthesis of Optically Active m-Phenylene PGl2 Derivative: Beraprost.

Hisanori Wakita

Hisanori Wakita

Basic Res. Lab., Toray Ind., Inc., Kamakura, Kanagawa 248, Japan

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Hideo Yoshiwara

Hideo Yoshiwara

Basic Res. Lab., Toray Ind., Inc., Kamakura, Kanagawa 248, Japan

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Hisao Nishiyama

Hisao Nishiyama

Basic Res. Lab., Toray Ind., Inc., Kamakura, Kanagawa 248, Japan

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Hiroshi Nagase

Hiroshi Nagase

Basic Res. Lab., Toray Ind., Inc., Kamakura, Kanagawa 248, Japan

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First published: 03 June 2010

Abstract

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ChemInform Abstract

The synthesis of Beraprost as well as its diastereomers [demonstrated for one isomer (XII)] is described. Key steps of the synthesis are the introduction of side chains by Prins reaction, Wittig reaction, and Wadsworth reaction. By variation of the starting cyclopentanobenzofuran [(I) or its enantiomer] as well as variation of the Wadsworth reagent (X), four diastereomers of the title compound are accessible.

chemical structure image

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