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dc.contributor.authorLoughlin, Wendy
dc.contributor.authorHaynes, Richard K.
dc.date.accessioned2019-05-12T22:46:52Z
dc.date.available2019-05-12T22:46:52Z
dc.date.issued1995
dc.identifier.issn00223263
dc.identifier.doi10.1021/jo00109a009
dc.identifier.urihttp://hdl.handle.net/10072/120255
dc.description.abstractA highly efficient four-step approach to the racemic CD-intermediate 8 from the racemic hydrindenone 10 has been developed. In the key step, the hydrindenone 10 is converted stereoselectively into the (±)-bromohydrindenone 17. Oxygen transposition from C-9 to C-8 is effected by means of conversion of 17 to the epoxide 20 and regioselective reductive ring opening of 20 with DIBALH. The resulting (±)-hydrindanol 8 was converted by the Homer—Wittig reaction with -methacrolein into the diene 24, hydrogenation of which provided the racemic hydrindanol 25. This is a direct precursor of racemic Grundmann’s ketone 9 and bears the alkyl side chain and the correct relative configuration at C13, C14, C17, and C20 of Vitamin D.
dc.description.peerreviewedYes
dc.languageEnglish
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.publisher.placeUSA
dc.relation.ispartofpagefrom807
dc.relation.ispartofpageto812
dc.relation.ispartofissue4
dc.relation.ispartofjournalJournal of Organic Chemistry
dc.relation.ispartofvolume60
dc.subject.fieldofresearchChemical Sciences
dc.subject.fieldofresearchMedicinal and Biomolecular Chemistry
dc.subject.fieldofresearchOrganic Chemistry
dc.subject.fieldofresearchcode03
dc.subject.fieldofresearchcode0304
dc.subject.fieldofresearchcode0305
dc.titleAn Efficient Stereoselective Synthesis of a Racemic CD-intermediate of Vitamin D
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.hasfulltextNo Full Text
gro.griffith.authorLoughlin, Wendy A.


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