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Diastereoselective Reduction of Bicyclic ‐Enamino Carbonyl Piperidines – Application to the Total Synthesis of (–)‐Deoxocassine
Author(s) -
Noël Romain,
VanucciBacqué Corinne,
FargeauBellassoued MarieClaude,
Lhommet Gérard
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600777
Subject(s) - chemistry , piperidine , bicyclic molecule , reduction (mathematics) , total synthesis , carbonyl group , stereochemistry , organic chemistry , mathematics , geometry
Abstract The chemo‐ and diastereoselective reduction of chiral piperidine β‐enamino esters 4 and 6 and β‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)