Diastereoselective reduction of bicyclic beta-enamino carbonyl piperidines application to the total synthesis of (-)-deoxocassine

The chemo- and diastereoselective reduction of chiral piperidine beta-enamino esters 4 and 6 and beta-enamino ketones 5 and 7 was studied and found to afford 2,3- or 2,3,6-substituted piperidines. This approach was successfully applied to the total synthesis of (-)-deoxocassine. ((c) Wiley-VCH Verla...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2007; no. 3; pp. 476 - 486
Main Authors Noel, Romain, Vanucci-Bacque, Corinne, Fargeau-Bellassoued, Marie-Claude, Lhommet, Gerard
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.01.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENANTIOPURE
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
STEREOSELECTIVE REDUCTION
PYRIDINE
diastereoselectivity
(-)-deoxocassine
nitrogen heterocycles
ESTERS
GENERAL-APPROACH
reduction
DERIVATIVES
ALKALOIDS
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Summary:The chemo- and diastereoselective reduction of chiral piperidine beta-enamino esters 4 and 6 and beta-enamino ketones 5 and 7 was studied and found to afford 2,3- or 2,3,6-substituted piperidines. This approach was successfully applied to the total synthesis of (-)-deoxocassine. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200600777