Stereoselective intramolecular nitrone cycloaddition in the synthesis of lasubine II

RW Hoffmann, A Endesfelder

Index: Hoffmann, Reinhard W.; Endesfelder, Andreas Liebigs Annalen der Chemie, 1986 , # 11 p. 1823 - 1836

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Citation Number: 13

Abstract

Abstract The intramolecular cycloaddition of α-substituted N-alkenylnitrones 2 leads to the 7- oxa-1-azanorbornanes 6, 7, and 8 with a selectivity of ca. 80% in favor of the exo, exo- disubstituted compound 6. The latter can be reduced to give the all-cis-2, 6-disubstituted 4- hydroxypiperidines 4 which are key compounds for the synthesis of certain alkaloids as demonstrated by the synthesis of lasubine II.