Journal
TETRAHEDRON LETTERS
Volume 46, Issue 48, Pages 8279-8283Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.09.163
Keywords
ciguatoxin CTX3C; natural product synthesis; reductive ring-opening; oxidative cyclization
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The C42-C52 part of ciguatoxin CTX3C (1) was synthesized from tri-O-acetyl D-glucal. The synthetic segment had a tetrahydropyran ring corresponding to the 'C49-reduced' L-ring of 1, designed to avoid side reactions due to acid-labile C49 acetal carbon during acidic reductive conditions planned in further synthesis toward 1. The vicinal dimethyl part at C47-C48 was constructed by a stepwise conjugate addition/methylation procedure. The C50-C52 unit was installed by Grignard addition of the C-3 unit followed by of the spirocyclic acetal. Stereoselective assembly of the C42-C44 part was achieved by Brown's asymmetric crotylboration. (c) 2005 Elsevier Ltd. All rights reserved.
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