Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide

被引：9

作者：

Chakraborty, Joy ^{[1
]}

Nanda, Samik ^{[1
]}

机构：

[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 31期

关键词：

RESORCYLIC ACID LACTONES; STEREOSELECTIVE TOTAL-SYNTHESIS; HSP90; ALLYLBORATION; BIOSYNTHESIS; CHEMISTRY; ALDEHYDES; BIOLOGY;

D O I：

10.1039/c9ob01504c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The convergent total synthesis of naturally occurring paecilomycin C is described here for the first time. Asymmetric Brown allylation, E-selective cross metathesis, and a biomimetic carboxylate assisted intramolecular nucleophilic ring opening of an epoxide were employed to access the enantiopure gamma-lactone framework of the natural product. Late stage E-selective Julia-Kocienski olefination was then employed to furnish the natural product in an efficient way.

引用

页码：7369 / 7379

页数：11

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