Asymmetric Total Synthesis of Apratoxin D

被引：27

作者：

Robertson, Bradley D. ^{[1
]}

Wengryniuk, Sarah E. ^{[1
]}

Coltart, Don M. ^{[1
]}

机构：

[1] Univ Houston, Dept Chem, Houston, TX 77204 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 20期

基金：

美国国家科学基金会;

关键词：

ALPHA-ALKYLATION; CYCLODEPSIPEPTIDE; KETONES; POTENT; ALPHA; ALPHA-BISALKYLATION;

D O I：

10.1021/ol302309c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric total synthesis of the marine natural product apratoxin D, a highly potent inhibitor of H-460 human lung cancer cell growth (IC50 value of 2.6 nM), is described. Asymmetric N-amino cyclic carbamate (ACC) alpha,alpha-bisalkylation was utilized to establish the isolated C-37 methyl group with excellent selectivity. Other key asymmetric transformations employed were an Evans syn-aldol and a Paterson anti-aldol, both of which also proceeded with excellent stereoselectivity.

引用

页码：5192 / 5195

页数：4

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