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

✍ Scribed by Michael Z. Hoemann; Konstantinos A. Agrios; Jeffrey Aubé

Book ID
104207793
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
865 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

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).

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Total synthesis of curacin A
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