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Perkin Transactions 1 ceased publication in 2002. Organic & Biomolecular Chemistry is the RSC's journal for high-quality, original organic chemistry research.
School of Chemistry, The University of Nottingham, Nottingham, UK
E-mail: . E-mail: gp@nottingham.ac.uk
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J. Chem. Soc., Perkin Trans. 1, 2002, 2243-2250
DOI:
10.1039/B206796J
Received
11 Jul 2002,
Accepted
13 Aug 2002
First published online
26 Sep 2002
A concise total synthesis of (+)-curacin A, a potent antimitotic agent isolated from the cyanobacterium Lyngbya majuscula, is described. The synthesis features a new strategy to the 2-cyclopropyl-4-alkenyl substituted thiazoline unit in the natural product involving facile and selective thioacylation of the amino-alcohol 10 with the benzotriazole derived thioamide 11, leading to 28, as a key step. Cyclodehydration of 28 using Burgess' reagent then completed the synthesis of curacin A 1.