Total synthesis of (+)-curacin A, a marine cytotoxic agent

The total synthesis of curacin A, a cytotoxic agent that interacts with the colchicine binding site on tubulin, is described. The convergent synthesis utilizes natural product and chiral pool starting materials (geraniol, serine) and asymmetric synthesis (chiral allylborane addition, Charette cyclop...

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Bibliographic Details
Published in:Tetrahedron 1997-08, Vol.53 (32), p.11087-11098
Main Authors: Hoemann, Michael Z., Agrios, Konstantinos A., Aubé, Jeffrey
Format: Article
Language:English
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Summary:The total synthesis of curacin A, a cytotoxic agent that interacts with the colchicine binding site on tubulin, is described. The convergent synthesis utilizes natural product and chiral pool starting materials (geraniol, serine) and asymmetric synthesis (chiral allylborane addition, Charette cyclopropanation) to procure the various chiral fragments in enantiomerically pure form. The assembly of the natural product involves carbon-carbon bond formation (Julia coupling) and heterocycle preparation (Wipf thiazoline synthesis). An asymmetric synthesis of curacin A, an inhibitor of tubulin polymerization, is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00368-2