Synthesis of the Pyranonaphthoquinones
Dehydroherbarin, (+)-Astropa­quinone B and (+)-Astropaquinone
C en Route to Ascomycones A and B

Andrew D. Wadsworth; Jonathan Sperry; Margaret A. Brimble

doi:10.1055/s-0029-1218832

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Synthesis 2010(15): 2604-2608
DOI: 10.1055/s-0029-1218832

PAPER

Synthesis of the Pyranonaphthoquinones Dehydroherbarin, (+)-Astropaquinone B and (+)-Astropaquinone C en Route to Ascomycones A and B

Andrew D. Wadsworth, Jonathan Sperry, Margaret A. Brimble*
Department of Chemistry, University of Auckland, 23 Symonds St., Auckland 1142, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;

Further Information

Publication History

Received 15 April 2010
Publication Date:
18 June 2010 (online)

Abstract
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Abstract

The total syntheses of the pyranonaphthoquinone natural products dehydroherbarin, (+)-astropaquinone B and (+)-astropaquinone C are described. A late stage oxidation strategy employed for the synthesis of the astropaquinones was not amenable to the conversion of dehydroherbarin into the ascomycones. The syntheses of astropaquinones B and C reported herein constitute the first total syntheses and their absolute stereochemistry was determined to be (1R,3S).

Key words

pyranonaphthoquinone - ascomycone - astropaquinone - dehydroherbarin - thysanone - 3C-protease inhibitor

References

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