171864-80-5Relevant academic research and scientific papers
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines
Zhao, Shuo,Smith, Kirsten S.,Deveau, Amy Morin,Dieckhaus, Christine M.,Johnson, Michael A.,Macdonald, Timothy L.,Cook, James M.
, p. 1559 - 1562 (2002)
Tryprostatin A 1 and B 2 are indole alkaloid-based fungal products that act in the G2/M phase of the cell cycle. Tryprostatin A and B as well as their two enantiomers and four diastereomers have been synthesized via a common strategy. As a measure of cyto
Total synthesis of tryprostatin A and B as well as their enantiomers
Zhao, Shuo,Gan, Tong,Yu, Peng,Cook, James M.
, p. 7009 - 7012 (1998)
The 3-methylindoles 3a, 3b were convened into tryprostatin A (1a), B (1b) and their enantiomers 2a, 2b via prenylation at the indole 2-position by generation of the required 2-lithioindole derivatives (from 7a, 7b), followed by alkylation.
Enantiospecific synthesis of optically active 6-methoxytryptophan derivatives and total synthesis of tryprostatin A1
Gan,Liu,Yu,Zhao,Cook
, p. 9298 - 9304 (1997)
A concise preparation of optically active L or D-6-methoxytryptophan ethyl ester 21 was developed via the Fischer indole/Schollkopf from 6- methoxy-3-methylindole 16 (four steps, 58% overall yield). This method was extended to the enantiospecific total sy
Enantiospecific total synthesis of tryprostatin A
Gan, Tong,Cook, James M.
, p. 1301 - 1304 (1997)
The 3-methyl-6-methoxyindole 3 was converted into tryprostatin A (1) via a regiospecific bromination process coupled with the Schollkopf chiral auxillary 7 to provide the 2-bromo-6-methyoxytryptophan 8a as a key intermediate.
Synthesis of tryptophan-containing 2,5-diketopiperazinesviasequential C-H activation: total syntheses of tryprostatin A, maremycins A and B
Qi, Wei-Yi,Shi, Bing-Feng,Yin, Xue-Song
, p. 13137 - 13143 (2021/10/21)
Indole 2,5-diketopiperazines (DKPs) are an important type of metabolic cyclic dipeptides containing a tryptophan (Trp) unit possessing a range of interesting biological activities. The intriguing structural features and divergent activities have stimulated tremendous efforts towards their efficient synthesis. Herein, we report the development of a unified strategy for the synthesis of three Trp-containing DKPs, namely tryprostatin A, and maremycins A and B,viaa sequential C-H activation strategy. The key Trp skeletons were synthesized from the inexpensive, readily available alanineviaa Pd(ii)-catalyzed β-methyl C(sp3)-H monoarylation. A subsequent C2-selective prenylation of the resulting 6-OMe-Trp by Pd/norbornene-promoted C-H activation led to the total synthesis of tryprostatin A in 12 linear steps from alanine with 25% overall yield. Meanwhile, total syntheses of maremycins A and B were successfully accomplished using a sequential Pd-catalyzed methylene C(sp3)-H methylation as the key step in 15 linear steps from alanine.
Total synthesis of tryprostatins A and B
Yamakawa, Takayuki,Ideue, Eiji,Iwaki, Yuzo,Sato, Ayumu,Tokuyama, Hidetoshi,Shimokawa, Jun,Fukuyama, Tohru
experimental part, p. 6547 - 6560 (2011/09/20)
Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fuerstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.
Total synthesis of tryprostatins a and b
Yamakawa, Takayuki,Ideue, Eiji,Shimokawa, Jun,Fukuyama, Tohru
supporting information; experimental part, p. 9262 - 9265 (2011/02/25)
A reasonable approach to the radical: The establishment of reliable conditions for the radical-mediated construction of indoles enabled the highly efficient synthesis of tryprostatins A and B. Use of the radical initiator 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) has allowed to carry out the radical cyclization at just 30°C, thereby suppressing the formation of by-products. Copyright
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein
Jain, Hiteshkumar D.,Zhang, Chunchun,Zhou, Shuo,Zhou, Hao,Ma, Jun,Liu, Xiaoxiang,Liao, Xuebin,Deveau, Amy M.,Dieckhaus, Christine M.,Johnson, Michael A.,Smith, Kirsten S.,Macdonald, Timothy L.,Kakeya, Hideaki,Osada, Hiroyuki,Cook, James M.
, p. 4626 - 4651 (2008/09/21)
Tryprostatin A is an inhibitor of breast cancer resistance protein, consequently a series of structure-activity studies on the cell cycle inhibitory effects of tryprostatin A analogues as potential antitumor antimitotic agents have been carried out. These
