106211-91-0Relevant articles and documents
TREMORGENIC MYCOTOXINS: SYNTHESIS OF 6-DEMETHOXYFUMITREMORGIN C
O'Malley, Gerard J.,Cava, Michael P.
, p. 1131 - 1134 (1987)
Synthetic studies directed toward the development of a general route to the fumitremorgin group of mycotoxins are disclosed.A chloroformate-induced cyclization of a L-tryptophan imine afforded an 1,2,3,4-tetrahydro-β-carboline which was elaborated to 6-demethoxyfumitremorgin C.
Concise synthesis of the cell cycle inhibitor demothoxyfumitremorgin C
Wang, Haishan,Ganesan, Arasu
, p. 4327 - 4328 (1997)
Reaction of the imine derived from L-tryptophan methyl ester and senecialdehyde with Fmoc-L-Pro-Cl induces an acyliminium Pictet-Spengler condensation, yielding a mixture of cis and trans tetrahydro-β-carbolines. Deprotection of the cis product with concomitant diketopiperazine formation afforded the natural product in 20% overall yield.
Mg(ClO4)2-catalyzed intramolecular allylic amination: Application to the total synthesis of demethoxyfumitremorgin C
Jiang, Danfeng,Xu, Zhengren,Jia, Yanxing
experimental part, p. 4225 - 4232 (2012/07/14)
A Mg(ClO4)2-catalyzed intramolecular amination of allylic alcohols with carbamate or sulfonamide nucleophiles to form substituted piperidine and pyrrolidine derivatives has been developed. This method has been successfully applied to the total synthesis of demethoxyfumitremorgin C.
