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
收藏
页码：1934 / 1937
页数：4
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