Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/79245
Type: Artigo de periódico
Title: Synthesis of methyl dihydrohardwickiate and its C-4 epimer. Structural amendment of natural crolechinic acid
Author: Costa, M
Perles, EC
Fujiwara, FY
Imamura, PM
Abstract: Reduction of the alpha,beta-unsaturated ester moiety of (+)-methyl hardwickiate with magnesium in methanol afforded methyl (4aS,6S,8aS, 1R,5R)-5,6,8a-trimethyl-5-[2'-(3 '-oxoyl)-ethyl-perhydro-1-naphthalenyl]-carboxaylate, while reduction with sodium in n-propanol, followed by esterification with diazomethane, furnished its C-4 epimer. After comparison of thr H-1- and C-13-NMR data of these compounds with those reported for crolechinic acid isolated from Croton lechleri, a stereochemical revision for the natural product is suggested. (C) 2000 Elsevier Science Ltd. All rights reserved.
Subject: reduction
(+)-methyl hardwickiate
stereochemistry
crolechinic acid
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Rights: fechado
Identifier DOI: 10.1016/S0031-9422(99)00583-X
Date Issue: 2000
Appears in Collections:Unicamp - Artigos e Outros Documentos

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