Synthesis of (+)-Leucascandrolide A Macrolactone

P. A. Evans; W. J. Andrews

doi:10.1055/s-0028-1087605

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Synfacts 2009(2): 0118-0118
DOI: 10.1055/s-0028-1087605

Synthesis of Natural Products and Potential Drugs

Synthesis of (+)-Leucascandrolide A Macrolactone

Contributor(s): Philip Kocienski, Indu Dager
P. A. Evans*, W. J. Andrews
The University of Liverpool, UK and Indiana University, Bloomington, USA

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Publication History

Publication Date:
22 January 2009 (online)

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Significance

Leucascandrolide A was isolated from the sponge Leucascandra caveolata and shows cytotoxic activity against KB (throat epithelial cancer), P388 (murine leukemia) and also antifungal activity against Candida albicans. This convergent synthesis of Leucascandrolide A macrolactone assembles the 1,5-bis(tetrahydropyran) moiety in E in a one-pot diastereoselective sequential two-component etherification followed by oxa-conjugate addition.