A versatile strategy for divergent and diastereoselective synthesis of natural product-like polyhydroxylated indolizidines

作者：Jiang Xiao Ping; Cheng Ying^*; Shi Gao Feng; Kang Zhi Mei

来源：Journal of Organic Chemistry, 2007, 72(6): 2212-2215.

DOI：10.1021/jo0624290

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 alpha,beta-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.

• 出版日期2007-3-16
• 单位北京师范大学