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Synfacts 2007(3): 0240-0240  
DOI: 10.1055/s-2007-968193
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Mitorubrin

Contributor(s): Philip Kocienski
J. Zhu, J. A. Porco, Jr.*
Boston University, USA
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

The salient features of the Porco synthesis of (-)-mitorubrin are (1) the Cu(I)-mediated enantioselective oxidative dearomatization of the o-alkynylbenzaldehyde C (er > 98:2) and (2) the Cu(I)-catalyzed cycloisomerization of the vinylogous carboxylic acid E to give the mitorubrin core in 58% yield for the two steps.