Stereodivergent Approach to Enantiopure Hydroxyindolizidines Through 1, 3??Dipolar Cycloaddition of 3??Hydroxypyrroline N??Oxide Derivatives

FM Cordero, F Pisaneschi, M Gensini…

Index: Cordero, Franca M.; Pisaneschi, Federica; Gensini, Martina; Goti, Andrea; Brandi, Alberto European Journal of Organic Chemistry, 2002 , # 12 p. 1941 - 1951

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Citation Number: 8

Abstract

Abstract The (3S)-3-alkoxypyrroline N-oxides 7 and 27 were easily prepared from L-malic acid and used as starting materials for enantiospecific syntheses of stereodifferentiated polyhydroxyindolizidines. Selection of the appropriate modality (inter-or intramolecular) for 1, 3-dipolar cycloaddition of the cyclic nitrone with 5-hydroxypentenoic acid derivatives gave access to either [1, 8a]-trans-or-cis-hydroxyindolizidines 31 and 24, respectively, through ...