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https://hdl.handle.net/2440/128494
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dc.contributor.author | Dissanayake, I. | - |
dc.contributor.author | Hart, J.D. | - |
dc.contributor.author | Becroft, E.C. | - |
dc.contributor.author | Sumby, C.J. | - |
dc.contributor.author | Newton, C.G. | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2020; 142(31):13328-13333 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.issn | 1520-5126 | - |
dc.identifier.uri | http://hdl.handle.net/2440/128494 | - |
dc.description.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. | - |
dc.description.statementofresponsibility | Isuru Dissanayake, Jacob D. Hart, Emma C. Becroft, Christopher J. Sumby and Christopher G. Newton | - |
dc.language.iso | en | - |
dc.publisher | ACS Publications | - |
dc.rights | © 2020 American Chemical Society | - |
dc.source.uri | http://dx.doi.org/10.1021/jacs.0c06306 | - |
dc.subject | Redox reactions; organic synthesis; reaction products; cyclization; chemical synthesis | - |
dc.title | Bisketene equivalents as diels-alder dienes | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/jacs.0c06306 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Dissanayake, I. [0000-0002-0233-8019] | - |
dc.identifier.orcid | Hart, J.D. [0000-0002-5318-518X] | - |
dc.identifier.orcid | Sumby, C.J. [0000-0002-9713-9599] | - |
dc.identifier.orcid | Newton, C.G. [0000-0002-8962-5917] | - |
Appears in Collections: | Aurora harvest 8 Chemistry and Physics publications |
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