A versatile strategy for divergent and diastereoselective synthesis of natural product-like polyhydroxylated indolizidines.
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.
Jiang
Xiao-Ping
XP
Chemistry Department, Beijing Normal University, Beijing 100875, China.
Cheng
Ying
Y
Shi
Gao-Feng
GF
Kang
Zhi-Mei
ZM
D000588:Amines / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis; D002264:Carboxylic Acids / Q000737:chemistry; D006865:Hydrogenation; D006900:Hydroxylation; D007212:Indolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000588:Amines; D001688:Biological Products; D002264:Carboxylic Acids; D007212:Indolizines