Synfacts 2009(2): 0118-0118  
DOI: 10.1055/s-0028-1087605
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

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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Publikationsverlauf

Publikationsdatum:
22. Januar 2009 (online)

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.