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A Versatile Strategy for Divergent and Diastereoselective Synthesis of Natural Product-Like Polyhydroxylated Indolizidines

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journal contribution
posted on 16.03.2007 by Xiao-Ping Jiang, Ying Cheng, Gao-Feng Shi, Zhi-Mei Kang
A general and versatile method for the divergent and diastereoselective synthesis of polyhydroxylated indolizidines has been established. The annulation reactions of a readily available enantiopure dihydroxylated cyclic secondary enamine with α,β-unsaturated carboxylates including methyl acrylate, methyl crotonate, methyl 2-hexenoate, allenoate, and dimethyl acetylenedicarboxylate and with malonyl chloride produced hexahydro- or tetrahydro-5-indolizinone-8-carboxylates in high yields. The resulting 5-indolizinone derivatives were converted into diverse polyhydroxylated indolizidines in good yields through practical hydrogenation and reduction reactions.