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Synlett 2009(8): 1273-1276  
DOI: 10.1055/s-0028-1088134
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

First Total Synthesis of Malvone A and Formal Syntheses of Boryquinone and Hybocarpone Using a Concise Strategy for Construction of Unsymmetrical Naphthoquinones

Kun-Liang Wu, Elysia P. M. T. Cohen, Yaodong Huang, Thomas R. R. Pettus*
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, CA, 93106-9510, USA
Fax: +1(805)8935690; e-Mail: pettus@chem.ucsb.edu;
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Publication History

Received 15 December 2008
Publication Date:
08 April 2009 (online)

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Abstract

The first total synthesis of malvone A (1) is presented in seven steps along with a nine-step formal synthesis of boryquinone (2) and an eleven-step formal synthesis of hybocarpone (3). The overall strategy, which accesses compounds 7-12 for the first time, employs an easily constructed α-tetralone, and it has significant implications for synthesis of the naphthoquinone portion of β-rubromycin (4) as well as a host of other unsymmetrical and differentially protected naphthoquinones.

Key words

naphthoquinone - o-quinone - natural product synthesis - total synthesis