159333-17-2Relevant academic research and scientific papers
The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C
Shangguan, Ning,Hehre, Warren J.,Ohlinger, William S.,Beavers, Mary Pat,Joullie, Madeleine M.
, p. 6281 - 6287 (2008)
The first total synthesis of roquefortine C is achieved by implementation of a novel elimination strategy to construct the thermodynamically unstable E-dehydrohistidine moiety. Molecular modeling studies are presented which explain the instability of the
ANALOGUES OF N-ACETYLARDEEMIN, METHOD OF PREPARATION AND USES THEREOF
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Figure 2, (2010/11/28)
The present invention provides a compound having the structure: wherein R1 R6 and R7 are independently hydrogen, OH, NH2, SH, halogen, C1-C9 linear or branched chain alkyl, alkylmercapto, alkylamino, dialkylamino, alkoxy, phenyl, etc.; wherein R0 and R2 are independently hydrogen, OH, linear or branched chain alkyl, -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4; wherein R3 and R4 are independently hydrogen, halogen, C1-C9 linear or branched chain alkyl, phenyl, etc.; wherein R5 is hydrogen, C1-C9 linear or branched chain alkyl, phenyl, etc.; and wherein R8 is hydrogen, C1-C9 linear or branched chain acyl, benzoyl, etc.; with the proviso that (a) when R2 is -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4, then R2 is hydrogen; (b) when R0 is -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4, then R2 is OH; and (c) when (i) R0 or R2 is -CR3R3-CH=CHR4, (ii) R3 and R5 are CH3 and (iii) R4 is hydrogen, then R1, R6 and R7 are not all hydrogen. Also provided are related compounds and compositions, and methods of inhibiting the growth of multidrug resistant cells by means of MDR reversal, collateral sensitivity and quantitative synergism.
On the reaction of tryptophan derivatives with N-phenylselenyl phthalimide: The nature of the kinetic and thermodynamic hexahydropyrrolo[2,3-b]indole products. Alkylation of tryptophan with inversion of configuration
Crich, David,Huang, Xianhai
, p. 7218 - 7223 (2007/10/03)
The cyclization of a range of tryptophan derivatives with N- phenylselenyl phthalimide leading to 3a-phenylselenyl-1,2,3,3a,8,8a- hexahydro[2,3-b]pyrroloindoles has been studied. It is established that in each case the kinetic diastereomer has the C-2 substituent on the exo face of the diazabicyclo-[3.3.0]octane skeleton, whereas the thermodynamic isomers have the C-2 substituent endo. A simple protocol for the alkylation of tryptophan, leading to α-substituted tryptophans with clean inversion of configuration, is presented.
The first total synthesis of roquefortine D
Chen, Wei-Chuan,Joullie, Madeleine M.
, p. 8401 - 8404 (2007/10/03)
The synthesis of roquefortine D (1), an alkaloid isolated from the cultures of Penicillium roqueforti, is described. The absolute stereochemistry of the natural product was determined by comparison of its optical rotation with that of the synthetic product. A photo-cleavable o- nitrobenzyl group was utilized for histidine side chain protection, and the cyclization to the diketopiperazine was carried out under mild conditions.
