An efficient sequential reaction process to polysubstituted indolizidines and quinolizidines and its application to the total synthesis of indolizidine 223A.
The reaction of iodides 1 with delta-chloropropylamines 5 in MeCN assisted with K2CO3 undergoes a sequential S(N)2/Michael addition/SN2/SN2 reaction process to give polysubstituted indolizidines and quinolizidines. Using this method, indolizidine 223A is synthesized from 2-ethyl-2-hexenoic acid in 12 linear steps and 14.5% overall yield. [Reaction: see text]
Zhu
Wei
W
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Dong
Dapeng
D
Pu
Xiaotao
X
Ma
Dawei
D