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Synthesis 2010(15): 2604-2608
DOI: 10.1055/s-0029-1218832
DOI: 10.1055/s-0029-1218832
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of the Pyranonaphthoquinones Dehydroherbarin, (+)-Astropaquinone B and (+)-Astropaquinone C en Route to Ascomycones A and B
Further Information
Received
15 April 2010
Publication Date:
18 June 2010 (online)
Publication History
Publication Date:
18 June 2010 (online)
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
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