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https://hdl.handle.net/2440/128494
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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 1520-5126 |
Statement of Responsibility: | 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 |
Published version: | http://dx.doi.org/10.1021/jacs.0c06306 |
Appears in Collections: | Aurora harvest 8 Chemistry and Physics publications |
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