Issue 28, 2012

Synthesis of anti-HIV lithospermic acid by two diverse strategies

Abstract

An efficient and convergent route for the synthesis of the natural product (+)-lithospermic acid, which possesses anti-HIV activity, was accomplished. The (±)-trans-dihydrobenzo[b]furan core therein was prepared by two different strategies. The first strategy involved the use of a palladium-catalyzed annulation to generate an appropriately substituted benzo[b]furan ester followed by a stereoselective reduction of a carbon–carbon double bond with Mg–HgCl2MeOH. The second strategy relied on an aldol condensation between a suitably substituted methyl arylacetate and 3,4-dimethoxybenzaldehyde, followed by cyclization. Finally, a total synthesis of (+)-lithospermic acid was completed via coupling of a trans-dihydrobenzo[b]furan cinnamic acid with an enantiomerically pure methyl lactate.

Graphical abstract: Synthesis of anti-HIV lithospermic acid by two diverse strategies

Supplementary files

Article information

Article type
Paper
Submitted
17 Mar 2012
Accepted
11 May 2012
First published
14 May 2012

Org. Biomol. Chem., 2012,10, 5456-5465

Synthesis of anti-HIV lithospermic acid by two diverse strategies

T. G. Varadaraju and J. R. Hwu, Org. Biomol. Chem., 2012, 10, 5456 DOI: 10.1039/C2OB25575H

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