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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 9
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Original Articles

Synthesis of Two Alnustone-Like Natural Diarylheptanoids via 4 + 3 Strategy

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Pages 1549-1562 | Received 16 Aug 2008, Published online: 02 Apr 2009
 

Abstract

The first total synthesis of (4E,6E)-1,7-bis(3,4-dihydroxyphenyl)-hepta-4,6-dien-3-one and an alternative synthesis of (4E,6E)-1,7-bis(4-hydroxyphenyl)-hepta-4,6-dien-3-one, two natural diarylheptanoids, mainly based on Claisen–Schmidt condensation were described. The crucial steps of the syntheses were the condensation of OH-protected 4-aryl-2-butanones with OH-protected 3-aryl-acrylaldehydes by the in situ enamination and then deprotection of OH groups to give the corresponding natural diarylheptanoids.

ACKNOWLEDGMENTS

We thank the Scientific and Technological Research Council of Turkey (TBAG-105T168) and Atatürk University for financial support of this work, Dr. Ebru Mete for elemental analysis, and Bilal Altundas for linguistic corrections.

Notes

Dedicated to Professor Metin Balcı on the occasion of his 60th birthday.

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