Absolute configuration and stereochemical analysis of 3α,6β-dibenzoyloxytropane

被引：15

作者：

Munoz, Marcelo A. ^{[2
]}

Martinez, Martina ^{[2
]}

Joseph-Nathan, Pedro ^{[1
]}

机构：

[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

[2] Univ Austral Chile, Fac Ciencias, Inst Ciencias Quim, Valdivia, Chile

来源：

PHYTOCHEMISTRY LETTERS | 2012年 / 5卷 / 03期

关键词：

VCD; HPLC polarimetric detection; Tropane alkaloids; Absolute configuration; 3; alpha; 6; beta-Dibenzoyloxytropane; VIBRATIONAL CIRCULAR-DICHROISM; TROPANE ALKALOIDS; ERYTHROXYLUM; 6-BETA-HYDROXYHYOSCYAMINE; DIASTEREOISOMERS; VALEROIDINE; PYRROLIDINE; PIPERIDINE; PYRIDINE;

D O I：

10.1016/j.phytol.2012.04.003

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Both enantiomers of 3 alpha,6 beta-dibenzoyloxytropane (1) have been prepared from optical active 6 beta-hydroxyhyoscyamines establishing their absolute configurations as ()-(3R,6R) and (+)-(3S,6S)-dibenzoyloxytropane. Independent stereochemical confirmation was obtained by vibrational circular dichroism measurements, since bands characteristic of (3R, 6R) and (3S, 6S) configurations of tropanediols derivatives were observed. In addition, a chiral HPLC method was developed for determining absolute configurations of tropane-related natural substances at the microgram (mu g) level. The complete H-1 NMR characterization of the scaffold of 1 is also reported. (C) 2012 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

引用

页码：450 / 454

页数：5

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