An efficient sequential reaction process to polysubstituted indolizidines and quinolizidines and its application to the total synthesis of indolizidine 223A |
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| Authors: | Zhu Wei Dong Dapeng Pu Xiaotao Ma Dawei |
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| Institution: | State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China. |
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| Abstract: | 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] |
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