A concise, total synthesis of the TMC-95A/B proteasome inhibitors.
作者： B. K. Albrecht , R. M. Williams
关键词:
摘要: A concise, total synthesis of the proteasome inhibitors TMC-95A/B has been accomplished. The features use an l-serine-derived E-selective modified Julia olefination reaction to ultimately control stereochemical outcome highly oxidized tryptophan fragment. Additionally, limited protecting groups at a late stage allowed for its completion in efficient manner.
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Jun Kohno, Yutaka Koguchi, Maki Nishio, Kazuya Nakao, Masataka Kuroda, Ryo Shimizu, Tetsuo Ohnuki, Saburo Komatsubara, Structures of TMC-95A-D: novel proteasome inhibitors from Apiospora montagnei sacc. TC 1093. Journal of Organic Chemistry. ,vol. 65, pp. 990- 995 ,(2000) , 10.1021/JO991375+
Sunil V. Pansare, John C. Vederas, Synthesis and reactivity of .beta.-lactones derived from L-threonine and related amino acids Journal of Organic Chemistry. ,vol. 54, pp. 2311- 2316 ,(1989) , 10.1021/JO00271A013
Norio. Miyaura, Akira. Suzuki, Palladium-catalyzed cross-coupling reactions of organoboron compounds Chemical Reviews. ,vol. 95, pp. 2457- 2483 ,(1995) , 10.1021/CR00039A007
Mangzhu Zhao, Jing Li, Eiichi Mano, Zhiguo Song, David M. Tschaen, Edward J. J. Grabowski, Paul J. Reider, Oxidation of Primary Alcohols to Carboxylic Acids with Sodium Chlorite Catalyzed by TEMPO and Bleach Journal of Organic Chemistry. ,vol. 64, pp. 2564- 2566 ,(1999) , 10.1021/JO982143Y
Songnian Lin, Samuel J. Danishefsky, The Total Synthesis of Proteasome Inhibitors TMC-95A and TMC-95B: Discovery of a New Method To Generate cis-Propenyl Amides Angewandte Chemie International Edition. ,vol. 41, pp. 512- 515 ,(2002) , 10.1002/1521-3773(20020201)41:3<512::AID-ANIE512>3.0.CO;2-R
Daniel B. Dess, J. C. Martin, A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species Journal of the American Chemical Society. ,vol. 113, pp. 7277- 7287 ,(1991) , 10.1021/JA00019A027
Masayuki Inoue, Hidetomo Furuyama, Hayato Sakazaki, Masahiro Hirama, Stereocontrolled synthesis of the northern part of potent proteasome inhibitor TMC-95A. Organic Letters. ,vol. 3, pp. 2863- 2865 ,(2001) , 10.1021/OL016303V
Alois Fürstner, Christof Brehm, Yolanda Cancho-Grande, Stereoselective synthesis of enamides by a Peterson reaction manifold. Organic Letters. ,vol. 3, pp. 3955- 3957 ,(2001) , 10.1021/OL016848P
Wanlong Jiang, Jutta Wanner, Richard J. Lee, Pierre-Yves Bounaud, Dale L. Boger, Total synthesis of the ramoplanin A2 and ramoplanose aglycon Journal of the American Chemical Society. ,vol. 124, pp. 5288- 5290 ,(2002) , 10.1021/JA020237Q
J. K. Stille, Y. Becker, Isomerization of N-allylamides and -imides to aliphatic enamides by iron, rhodium, and ruthenium complexes Journal of Organic Chemistry. ,vol. 11, pp. 2139- 2145 ,(1980) , 10.1021/JO01299A021