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A Simple Enantioselective Route to Functionalized Indolizidines: Synthesis of (+)‐Ipalbidine and (+)‐Antofine
Author(s) -
Pansare Sunil V.,
Lingampally Rajinikanth,
Dyapa Rajendar
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100125
Subject(s) - enantioselective synthesis , ketone , indolizidine , chemistry , nitro , alkene , organocatalysis , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , alkyl , alkaloid
An efficient route to functionalized indolizidines from an enantiomerically enriched γ‐nitro ketone is described. The nitro ketone is obtained by an organocatalytic, enantioselective ketone‐nitro alkene Michael addition. Oxidative ring expansion of the nitro ketone and subsequent methanolysis provides a 8‐nitro‐4‐oxooctanoate. This is stereoselectively transformed to the key, functionalized indolizidine intermediate which is readily converted to (+)‐ipalbidine and (+)‐antofine.