Synthesis of γ-Lactones via the Kowalski Homologation Reaction: Protecting-Group-Free Divergent Total Syntheses of Eupomatilones-2,5,6, and 3-epi-Eupomatilone-6

被引：14

作者：

Choi, Hosam ^{[1
]}

Jang, Hanho ^{[1
]}

Kim, Hyoungsu ^{[2
]}

Lee, Kiyoun ^{[1
]}

机构：

[1] Catholic Univ Korea, Dept Chem, Bucheon 14662, South Korea

[2] Ajou Univ, Coll Pharm, Suwon 16499, South Korea

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 19期

基金：

新加坡国家研究基金会;

关键词：

ASYMMETRIC ALDOL ADDITIONS; N-ACYL OXAZOLIDINONES; ESTER HOMOLOGATION; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; REDUCTIVE HOMOLOGATION; PUTATIVE STRUCTURE; BUTYROLACTONES; ACIDS; OXAZOLIDINETHIONES;

D O I：

10.1021/acs.orglett.9b02848

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient synthesis of functionalized chiral gamma-butyrolactone scaffolds has been described. The basis of the approach is the Kowalski ester homologation that is modified for our proposed transformation. The newly developed methodology combines a divergent synthetic strategy to permit a straightforward protecting-group-free asymmetric total syntheses of eupomatilones-2,5,6, and 3-epi-eupomatilone-6 in five or six steps from commercial starting materials, making it one of the shortest syntheses reported to date.

引用

页码：7857 / 7862

页数：6