Bisketene Equivalents as Diels-Alder Dienes

被引：19

作者：

Dissanayake, Isuru ^{[1
]}

Hart, Jacob D. ^{[1
]}

Becroft, Emma C. ^{[1
]}

Sumby, Christopher J. ^{[1
]}

Newton, Christopher G. ^{[1
]}

机构：

[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 31期

基金：

澳大利亚研究理事会;

关键词：

ENOL SILYL ETHERS; 2,5-BIS(TRIMETHYLSILOXY) FURANS; DERIVATIVES; CHEMISTRY; HYDROQUINONE; ANNELATION; GENERATION; QUINONES; KETENES; ROUTE;

D O I：

10.1021/jacs.0c06306

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of Para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (+/-)-indanostatin.

引用

页码：13328 / 13333

页数：6

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