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Short and stereoselective synthesis of (±)‐ibogamine via a Vinylsulfone intermediate, IV
Author(s) -
Herdeis Claus,
HartkeKarger Claudia
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910119
Subject(s) - stereoselectivity , chemistry , reagent , sulfone , cuprate , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , physics , optoelectronics , doping
Ibogamine ( 11b ) was synthesized starting from the vinyl sulfone 3 . Addition of organocuprate reagents to 3 furnished 2a–d with high stereoselectivity. Only products from the syn addition of the cuprate reagents could be detected. Functional group transformations provided 7a,b the key intermediates for the synthesis of (±)‐21‐noribogamine ( 11a ) and (±)‐ibogamine ( 11b ).