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Issue 18, 2001
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First highly stereoselective synthesis of (+)-dihydrosesamin, a trisubstituted tetrahydrofuran-type of lignan, by using highly erythro-selective aldol condensation

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Abstract

A 2,3,4-tri-substituted tetrahydrofuran-type lignan, (+)-dihydrosesamin 2, was stereoselectively synthesized by using erythro-selective aldol condensation of the potassium enolate from (3R)-3-(3,4-methylenedioxyphenyl)-4-butanolide 3 with piperonal as a key reaction. This is the first stereoselective synthesis of (+)-dihydrosesamin, which is the enantiomer of the natural product.

Graphical abstract: First highly stereoselective synthesis of (+)-dihydrosesamin, a trisubstituted tetrahydrofuran-type of lignan, by using highly erythro-selective aldol condensation

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Article information


Submitted
20 Jun 2001
Accepted
06 Aug 2001
First published
04 Sep 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2158-2160
Article type
Paper

First highly stereoselective synthesis of (+)-dihydrosesamin, a trisubstituted tetrahydrofuran-type of lignan, by using highly erythro-selective aldol condensation

S. Yamauchi, T. Tanaka and Y. Kinoshita, J. Chem. Soc., Perkin Trans. 1, 2001, 2158
DOI: 10.1039/B105419H

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