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Synfacts 2007(8): 0781-0781  
DOI: 10.1055/s-2007-968718
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Papulacandin D

Contributor(s): Philip Kocienski
S. E. Denmark*, C. S. Regens, T. Kobayashi
University of Illinois at Urbana-Champaign, USA
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

Papulacandin D is a potent antifungal agent. Highlights of the Denmark synthesis include (a) a Pd-catalyzed coupling of iodoarene C with the silanol B to generate the 2-arylglycal D and (b) the asymmetric allylation of aldehyde F mediated by the bisphosphoramide G (S. E. Denmark et al. J. Org. Chem. 2006, 71, 1513; J. Org. Chem. 2006, 71, 1523).