Total Synthesis of Chloptosin, a Potent Apoptosis-Inducing Cyclopeptide

被引：32

作者：

Yu, Shun-Ming ^{[1
]}

Hong, Wen-Xu ^{[1
]}

Wu, Yuan ^{[1
]}

Zhong, Chun-Long ^{[1
]}

Yao, Zhu-Jun ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 05期

关键词：

AMINO-ACID; ENANTIOSELECTIVE SYNTHESIS; PEPTIDE-SYNTHESIS; HIMASTATIN; CYCLOHEXAPEPTIDE; ANTIBIOTICS; CYCLIZATION; DEATH; CELLS;

D O I：

10.1021/ol100135a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A bidirectional total synthesis of chloptosin has been achieved in 16 operations (32 individual reactions) and 3% overall yield from the readily available materials. Palladium-catalyzed tryptophan synthesis, diastereoselective selenocyclization and oxidative deselenation successfully served as key steps in construction of the dimeric core amino acid. 2-Bromo-1-ethyl pyridinium tetrafluoroborate was efficiently employed in the peptide couplings with spatial encumbrance in this synthesis.

引用

页码：1124 / 1127

页数：4

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