An efficient synthesis of optically active physostigmine from tryptophan via alkylative cyclization.
[reaction: see text] A new and efficient synthetic route to physostigmine is described. Corey-Kim reagent reacted with tryptamine or tryptophan carbamates to give 3a-(methylthiomethyl)hexahydropyrrolo[2,3-b]indole skeletons. Formal total synthesis of racemic and chiral physostigmine was accomplished in excellent overall yields, in short steps.
Kawahara
M
M
Faculty of Pharmaceutical Sciences, Chiba University, Japan.
Nishida
A
A
Nakagawa
M
M
D000478:Alkylation; D055095:Optics and Photonics; D010830:Physostigmine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
D014364:Tryptophan; D010830:Physostigmine