A Chemoenzymatic Total Synthesis of the Protoilludane Aryl Ester (+)-Armillarivin

被引：33

作者：

Schwartz, Brett D. ^{[1
]}

Matousova, Eliska ^{[1
]}

White, Richard ^{[1
]}

Banwell, Martin G. ^{[1
]}

Willis, Anthony C. ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 08期

基金：

澳大利亚研究理事会;

关键词：

PASTEURESTIN-A; ROUTE; ASSIGNMENT; REDUCTION; STATE;

D O I：

10.1021/ol400583c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title natural product, 1, has been synthesized in 20 steps from the enantiomerically pure cis-1,2-dihydrocatechol 2, itself obtained through the whole-cell biotransformation of toluene. The pivotal steps in the reaction sequence involve a Diels-Alder cycloaddition reaction between diene 2 and cyclopentenone (3) and the photochemically promoted 1,3-acyl rearrangement of the bicyclo[2.2.2]oct-4-en-1-one 20 derived from the cycloadduct 4.

引用

页码：1934 / 1937

页数：4

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