Furan Oxidation Strategy for the Synthesis of the Macrolactone Analogue of Migrastatin

被引：3

作者：

Airan, Yougant ^{[1
]}

Prasad, Kavirayani R. ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 22期

关键词：

ASYMMETRIC ALDOL ADDITIONS; FORMAL SYNTHESIS; MACROLIDE CORE;

D O I：

10.1021/acs.joc.9b02413

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of the 14-membered macrolide core of migrastatin is accomplished by the use of fury' carbinol in 13 linear steps from furfural with similar to 11% overall yield. Key strategies in the synthesis include the oxidative ring opening of furan and its use as a four-carbon synthon, S(N)2 displacement of a functionalized ally' bromide, and ring closing metathesis to obtain the macrolactone.

引用

页码：14974 / 14979

页数：6