Medium-Sized Cyclic Ethers via Stevens [1,2]-Shift of Mixed Monothioacetal-Derived Sulfonium Ylides: Application to Formal Synthesis of (+)-Laurencin

被引：30

作者：

Lin, Rongrong ^{[1
]}

Cao, Liya ^{[1
]}

West, F. G. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, E3-43 Gunning Lemieux Chem Ctr, Edmonton, AB T6G 2G2, Canada

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 03期

基金：

加拿大自然科学与工程研究理事会;

关键词：

MEDIUM RING ETHERS; OXONIUM YLIDES; ENANTIOSELECTIVE SYNTHESIS; CLOSURE REACTIONS; REARRANGEMENT; CONSTRUCTION; HETEROATOM; EXPANSION; 1,3-OXATHIOLANES; DERIVATIVES;

D O I：

10.1021/acs.orglett.6b03719

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach to medium-sized cyclic ethers was devised using a Stevens [1,2]-shift of a sulfonium ylide derived from a readily accessible six-membered mixed-monothioacetal precursor. The concise and efficient transformation offers a surprising degree of chirality transfer with observed retention of stereochemical configuration on the anomeric migrating carbon and has been applied as the key step in an enantioselective formal synthesis of (+)-laurencin.

引用

页码：552 / 555

页数：4