Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4

被引：1

作者：

Richardson, Melodie S. W. ^{[1
]}

Tame, Christopher J. ^{[2
]}

Poole, Darren L. ^{[2
]}

Donohoe, Timothy J. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Mansfield Rd, Oxford OX1 3TA, England

[2] GlaxoSmithKline Med Res Ctr, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England

来源：

CHEMICAL SCIENCE | 2019年 / 10卷 / 25期

基金：

英国工程与自然科学研究理事会;

关键词：

STEREOCONTROLLED CYCLIZATION; ANOMALOUS ENANTIOSELECTIVITY; ALKOXIDE PRECOORDINATION; FACIAL SELECTIVITY; PART II; SYSTEM; ABC; EPI-(+)-DUOCARMYCIN; (+)-DUOCARMYCIN; HYDROGENATION;

D O I：

10.1039/c9sc01761e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Our synthesis of the CDE ring fragment of pectenotoxin-4 utilised two key steps to make the complex bicyclic ketal unit: (i) a rhodium-catalysed vinyl group 1,4-addition as the major C-C bond forming step; (ii) a stereoselective Sharpless Asymmetric Dihydroxylation (SAD) of the resulting 1,1-disubstituted homoallylic alcohol. Subsequent acid-catalysed cyclisation afforded the desired [5,6]-bicyclic ketal of the target molecule. This methodology was shown to be compatible with the desired E ring fragment 35 in order to construct the CDE fragment 37 of pectenotoxin-4.

引用

页码：6336 / 6340

页数：5