Volume 25, Issue 35
Natural Products
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ChemInform Abstract: New Asymmetric Synthesis of (-)-Esermethole.

M. PALLAVICINI

M. PALLAVICINI

Ist. Chim. Farm. Tossicol., Univ. Milano, I-20131 Milano, Italy

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E. VALOTI

E. VALOTI

Ist. Chim. Farm. Tossicol., Univ. Milano, I-20131 Milano, Italy

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L. VILLA

L. VILLA

Ist. Chim. Farm. Tossicol., Univ. Milano, I-20131 Milano, Italy

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I. RESTA

I. RESTA

Ist. Chim. Farm. Tossicol., Univ. Milano, I-20131 Milano, Italy

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First published: August 30, 1994

Abstract

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ChemInform Abstract

(-)-Esermethole (-)-(XII) and (+)-esermethole are synthesized with a good degree of stereoselectivity (up to 63% d.e.) by use of the (S)- phenylethylamine (S)-(VIII) and its (R)-enantiomer as chiral alkylating agents, respectively. The use of (-)-menthyl chloroacetate as chiral aklylating agent under different reaction conditions (temp., solvent and base) only leads to moderate degrees of stereoselectivity ( 1-49% d.e.).

chemical structure image

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