[4 + 1] cycloaddition of bis(alkylthio)carbenes with vinyl isocyanates. Total synthesis of (+/-)-mesembrine.
[reaction: see text] The Sceletium alkaloid mesembrine has been synthesized in 13% overall yield by a sequence featuring a [4 + 1] cycloaddition of a bis(alkylthio)carbene with a functionalized vinyl isocyanate.
Rigby
J H
JH
Department of Chemistry, Wayne State University, Detroit, MI 48202-3489, USA. jhr@chem.wayne.edu
Dong
W
W
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D026121:Indole Alkaloids; D017953:Isocyanates / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry
D000470:Alkaloids; D005609:Free Radicals; D026121:Indole Alkaloids; D017953:Isocyanates; D011760:Pyrrolidinones; C011300:mesembrine