Enchaînements hétéroatomiques et leurs produits de cyclisation. VI. Nouvelle synthèse de céphèmes: acétyl-3 méthyl-7 phtalimido-7 oxo-8 thia-5 aza-1 bicyclo[4.2.0]octènes-2 diastéréomères

The total synthesis of two diastereomeric cephems is described with three original steps in excellent yields: construction of the 1,3-thiazine ring via a (4+2) cycloaddition reaction, regioselective hydrogenation of the carbon–nitrogen double bond, and lactamization using BOP.

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Bibliographic Details
Published in:Canadian journal of chemistry 1983-06, Vol.61 (6), p.1169-1175
Main Authors: Rozé, Jean-Claude, Pradere, Jean-Paul, Duguay, Guy, Guevel, André, Quiniou, Hervé, Poignant, Serge
Format: Article
Language:English
Online Access:Get full text
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Description
Summary:The total synthesis of two diastereomeric cephems is described with three original steps in excellent yields: construction of the 1,3-thiazine ring via a (4+2) cycloaddition reaction, regioselective hydrogenation of the carbon–nitrogen double bond, and lactamization using BOP.
ISSN:0008-4042
1480-3291
DOI:10.1139/v83-209