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Synfacts 2009(3): 0279-0279  
DOI: 10.1055/s-0028-1087690
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Hypocrellin A

Contributor(s): Philip Kocienski, Stewart Eccles
E. M. O’Brien, B. J. Morgan, M. C. Kozlowski*
University of Pennsylvania, Philadelphia, USA
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

Hypocrellin A is a perylenequinone from Shiraia bambusicola that displays light-­induced activity against tumor cell lines. The ­synthesis features (1) a catalytic enantioselective coupling of highly functionalized naphthols (B → D) and (2) creation of a seven-membered ring via a 1,8-diketone aldol reaction (G → H).