Formal Synthesis of Merrilactone A Using a Domino Cyanide 1,4-Addition-Aldol Cyclization

被引：34

作者：

Nazef, Naim ^{[1
]}

Davies, Robert D. M. ^{[3
]}

Greaney, Michael F. ^{[2
]}

机构：

[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[3] AstraZeneca, Mereside, Macclesfield SK10 4TG, Cheshire, England

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 14期

基金：

英国工程与自然科学研究理事会;

关键词：

ESTERS; ALDOL; ENANTIOMER;

D O I：

10.1021/ol301513h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal synthesis of merrilactone A has been completed using a domino 1,4-addition-aldol process as the key step. Both iodo- and cyano-1, 4-addition-aldol cyclizations were productive in forming the highly hindered C1-C9 bond linking vic-quaternary and tertiary stereocenters. The latter method was used to complete a formal total synthesis of the natural product.

引用

页码：3720 / 3723

页数：4

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