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.
A concise efficient route to fumitromorgins
Bailey, Patrick D.,Cochrane, Philip J.,Lorenz, Katrin,Collier, Ian D.,Pearson, David P.J.,Rosair, Georgina M.
, p. 113 - 115 (2001)
Using the kinetically controlled Pictet-Spengler reaction, we have developed a three-step, diastereoselective and enantiospecific synthesis of the natural product demethoxy-fumitremorgin C in 21% overall yield.
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.
Preparation method of anti-tumor active compound
-
, (2016/11/28)
The invention relates to a preparation method of a compound Demethoxyfumitremorgin C having anti-tumor activity. The preparation method includes the steps that L-tryptophan is used as a starting raw material and performs esterification reaction with isopropyl alcohol to obtain L-tryptophan isopropyl ester, then the L-tryptophan isopropyl ester is connection with senecioic acid to obtain amide, a dihydro beta-carboline intermediate is obtained through Bischler-Napieralski reaction, then a cis-tetrahydro beta-carboline intermediate is obtained by using sodium borohydride to reduce imine in a high selectivity mode, a protecting group is removed after connection with protected praline, intramolecular cyclization occurs to obtain the target compound Demethoxyfumitremorgin C (I). The raw material of the preparation method is cheap, the stereoselectivity and yield are high, and the preparation method is suitable for industrial production.
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.
Fumitremorgin C analogs that reverse mitoxantrone resistance in human colon carcinoma cells
He, Haiyin,Rabindran, Sridhar G.,Greenberger, Lee M.,Carter, Guy T.
, p. 424 - 437 (2007/10/03)
A series of diketopiperazines (1a) that mimic the natural product, fumitremorgin C (1), were synthesized. This class of compounds enhanced the sensitivity of a mitoxantrone-selected colon carcinoma cell line, S1-M1-3.2, to various antitumor agents, thereb
An Asymmetric Route to the Demethoxy-fumitremorgins
Bailey, Patrick D.,Hollinshead, Sean P.,McLay, Neil R.,Everett, Judith H.,Reynolds, Colin D.,et al.
, p. 451 - 458 (2007/10/02)
By use of a modified Pictet-Spengler reaction under conditions of kinetic control, the optically pure cis-1,3-disubstituted tetrahydro-β-carboline 21a was prepared from L-tryptophan; this generated a key tricyclic unit that possessed the correct relative
A STEREOSELECTIVE ENTRY TO THE FUMITREMORGINS
Bailey, Patrick D.,Hollinshead, Sean P.,McLay, Neil R.
, p. 6421 - 6422 (2007/10/02)
The reaction of (L)-tryptophan methyl ester with butynone yields a key cis-1,3-disubstituted-tetrahydro-β-carboline (3), simple modification of which gives access to the skeleton of the Fumitremorgin alkaloids.
