chloptosin 的全合成，一种强效诱导细胞凋亡的环肽。

Total synthesis of chloptosin, a potent apoptosis-inducing cyclopeptide.

机构信息

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

出版信息

Org Lett. 2010 Mar 5;12(5):1124-7. doi: 10.1021/ol100135a.

DOI:10.1021/ol100135a

PMID:20136143

Abstract

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.

摘要

已从易得的起始原料出发，经 16 步反应（32 个独立反应），以 3%的总产率实现了氯普斯汀的全合成的对映选择性构建。钯催化的色氨酸合成、非对映选择性硒环化和氧化脱硒反应成功作为构建二聚体核心氨基酸的关键步骤。在这个合成中，2-溴-1-乙基吡啶四氟硼酸盐在肽偶联中有效地利用了空间位阻。