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Formal Synthesis of (−)‐Aphanorphine Using Sequential Photomediated Radical Reactions of Dithiocarbamates
Author(s) -
Grainger Richard S.,
Welsh Emma J.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701055
Subject(s) - radical cyclization , chemistry , dithiocarbamate , alkyl , iminium , stereochemistry , organic chemistry , catalysis
Time to change the light bulb : An alkyl dithiocarbamate, itself formed through a photoinitiated group‐transfer cyclization of a carbamoyl radical, undergoes a second photomediated radical process initiated with a different light source. These two reactions, which proceed through the same cyclohexenyl radical intermediate, are key steps in a new asymmetric synthesis of the alkaloid aphanorphine. TEMPO=2,2,6,6‐tetramethyl‐1‐piperidinoxyl radical.
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