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Unusual endoperoxide isomerizations:: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides

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dc.contributor.authorErden, Ihsan
dc.contributor.authorOcal, Nuket
dc.contributor.authorSong, Jiangao
dc.contributor.authorGleason, Cindy
dc.contributor.authorGartner, Christian
dc.date.accessioned2026-06-27T13:05:31Z
dc.date.issued2006
dc.description.abstractAn unusual peroxide base-promoted isomerization is uncovered. Saturated endoperoxides derived from fulvenes give rise to 2-vinyl-2-cyclopentenones upon treatment with DBU in CH2CL2 in a one-pot reaction. This methodology is applied to a convenient synthesis of dihydrojasmone. Moreover, functional groups placed on the side chain at C-6 participate in the base-catalyzed isomerizations via conjugate attack at the enone moiety to give 2-cyclopentenones carrying oxygen heterocycles at C-2. (c) 2006 Elsevier Ltd. All rights reserved.en
dc.description.sponsorshipNIGMS NIH HHS [S06 GM052588] Funding Source: Medline
dc.description.urihttps://doi.org/10.1016/j.tet.2006.07.107
dc.identifier.doi10.1016/j.tet.2006.07.107
dc.identifier.endpage10682
dc.identifier.issn0040-4020
dc.identifier.issue46
dc.identifier.pubmed17998948
dc.identifier.startpage10676
dc.identifier.urihttps://hdl.handle.net/20.500.14981/49596
dc.identifier.volume62
dc.identifier.wos000241746100008
dc.language.isoeng
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.relation.ispartofTETRAHEDRON
dc.rightsopenAccess
dc.subjectDYE-SENSITIZED PHOTOOXYGENATION
dc.subjectSINGLET OXYGEN
dc.subjectALLENE OXIDE
dc.subjectSUCCINOIN DERIVATIVES
dc.subjectRING EXPANSION
dc.subject6,6-DIMETHYLFULVENE
dc.subjectCYCLOPENTENONES
dc.subjectREARRANGEMENT
dc.subjectOXIDATION
dc.subjectCHEMISTRY
dc.titleUnusual endoperoxide isomerizations:: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides
dc.typeArticle
dspace.entity.typePublication
local.import.sourceWOS

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