Tetrahedron Letters

Preparation and diels-alder reaction of N-carbomethoxy-5-ethyl-1.2-dihydropyridine: An approach for the synthesis of catharanthine

S Raucher, RF Lawrence

Index: Raucher, Stanley; Lawrence, Ross F. Tetrahedron Letters, 1983 , vol. 24, # 29 p. 2927 - 2930

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Citation Number: 33

Abstract

Abstract N-carbomethoxy-5-ethyl, 1, 2-dihydropyridine (1) may be prepared by the bromination of N-carbomethoxy-3-ethyl-1, 2, 5, 6-tetrahydropyridine (10), and subsequent double dehydrobromination with EtAlCl 2/HMPA; this diene undergoes Diels-Alder reaction with dimethyl methylenemalonate (2) to give the isoquinuclidine (3), an intermediate in our planned approach to catharanthine.