Total synthesis of (+/-) -phenserine via [4+1] cyclization of a bis(alkylthio)carbene and an indole isocyanate.
[structure: see text]. A total synthesis of acetylcholine blocking agent, phenserine, has been achieved by employing a [4+1] cyclization between an appropriately substituted indole isocyanate and a bis(alkylthio)carbene.
Rigby
James H
JH
Department of Chemistry, Wayne State University, Detroit, MI 48202-3489, USA. jhr@chem.wayne.edu
Sidique
Shyama
S
D003500:Cyclization; D006838:Hydrocarbons / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010830:Physostigmine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013440:Sulfides / Q000737:chemistry*
D006838:Hydrocarbons; D007211:Indoles; D017953:Isocyanates; D013440:Sulfides; C030011:carbene; D010830:Physostigmine; D008697:Methane; C092280:phenserine