Preparation of an Eight-Membered Sesquiterpene Lactone Resulting from Sequential Gif System GoAggIII and MCPBA Oxidation of ( )-10β,14-Dihydroxy-allo-aromadendrane 英文参考文献.docVIP
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Preparation of an Eight-Membered Sesquiterpene Lactone Resulting from Sequential Gif System GoAggIII and MCPBA Oxidation of ( )-10β,14-Dihydroxy-allo-aromadendrane 英文参考文献
Molecules 2005, 10, 1010-1014
molecules
ISSN 1420-3049
Preparation of an Eight-Membered Sesquiterpene Lactone
Resulting from Sequential Gif System GoAggIII and MCPBA
Oxidation of (+)-10β,14-Dihydroxy-allo-aromadendrane
Márcia M. L. de Bodas 1, Maria Rita Marques 2, Adilson Beatriz 1 and Dênis P. de Lima 1,*
1 Universidade Federal de Mato Grosso do Sul, Departamento de Química / CCET – CP 549 - 79070-
900 – Campo Grande (MS) – Brazil. Tel. +55 (67)-345-3578, Fax +55 (67) 345-3552
2 Universidade Federal de Mato Grosso do Sul, Departamento de Morfofisiologia / CCBS – CP 549 -
79070-900 – Campo Grande (MS) - Brazil
* Author to whom correspondence should be addressed; E-mail: dlima@nin.ufms.br
Received: 8 December 2004 / Accepted: 2 March 2005 / Published: 31 August 2005
Abstract: Studies aimed at a comparison of chemical, biomimetic (Gif system GoAggIII)
and enzymatic (CHMO) transformations of natural (+)-10β,14-dihydroxy-allo-
aromadendrane have led to preparation of an eight-member sesquiterpene lactone.
Keywords: (+)-10β,14-dihydroxy-allo-aromadendrane, (-)-allo-aromandendrone, apo-
aromadendrone, eight-member sesquiterpene lactone, GoAggIII, CHMO, MCPBA,
Baeyer-Villiger
Introduction
Our research group has been undertaking an effort to perform random transformations in natural
compounds with the purpose of obtaining novel, potentially bioactive derivatives. The sesquiterpene
(+)-10β,14-dihydroxy-allo-aromadendrane (1) (Figure 1), has already been target of different studies
reported by our group. Compound 1 is a natural product isolated from Pulicaria paludosa [1] and
Duguetia glabriuscula [2]. Investigations concerning chemical modification [3], microbial
transformation [4], electrolysis [5] and NMR assignments [6] of this molecule have demonstrated a
great reaction versatility leading to unique carbon frameworks.
Molecules 2005, 10
1011
Figure 1: (+)-10β,
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