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Type: Journal article
Title: Bisketene equivalents as diels-alder dienes
Author: Dissanayake, I.
Hart, J.D.
Becroft, E.C.
Sumby, C.J.
Newton, C.G.
Citation: Journal of the American Chemical Society, 2020; 142(31):13328-13333
Publisher: ACS Publications
Issue Date: 2020
ISSN: 0002-7863
Statement of
Isuru Dissanayake, Jacob D. Hart, Emma C. Becroft, Christopher J. Sumby and Christopher G. Newton
Abstract: 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.
Keywords: Redox reactions; organic synthesis; reaction products; cyclization; chemical synthesis
Rights: © 2020 American Chemical Society
DOI: 10.1021/jacs.0c06306
Appears in Collections:Aurora harvest 8
Chemistry and Physics publications

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