Diastereoselective Reduction of Bicyclic ‐Enamino Carbonyl Piperidines – Application to the Total Synthesis of (–)‐Deoxocassine | Zendy

Noël Romain | Zendy; VanucciBacqué Corinne | Zendy; FargeauBellassoued MarieClaude | Zendy; Lhommet Gérard | Zendy

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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

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)

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