dc.contributor.author | Loughlin, Wendy | |
dc.contributor.author | Haynes, Richard K. | |
dc.date.accessioned | 2019-05-12T22:46:52Z | |
dc.date.available | 2019-05-12T22:46:52Z | |
dc.date.issued | 1995 | |
dc.identifier.issn | 00223263 | |
dc.identifier.doi | 10.1021/jo00109a009 | |
dc.identifier.uri | http://hdl.handle.net/10072/120255 | |
dc.description.abstract | A 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.peerreviewed | Yes | |
dc.language | English | |
dc.language.iso | eng | |
dc.publisher | American Chemical Society | |
dc.publisher.place | USA | |
dc.relation.ispartofpagefrom | 807 | |
dc.relation.ispartofpageto | 812 | |
dc.relation.ispartofissue | 4 | |
dc.relation.ispartofjournal | Journal of Organic Chemistry | |
dc.relation.ispartofvolume | 60 | |
dc.subject.fieldofresearch | Chemical Sciences | |
dc.subject.fieldofresearch | Medicinal and Biomolecular Chemistry | |
dc.subject.fieldofresearch | Organic Chemistry | |
dc.subject.fieldofresearchcode | 03 | |
dc.subject.fieldofresearchcode | 0304 | |
dc.subject.fieldofresearchcode | 0305 | |
dc.title | An Efficient Stereoselective Synthesis of a Racemic CD-intermediate of Vitamin D | |
dc.type | Journal article | |
dc.type.description | C1 - Articles | |
dc.type.code | C - Journal Articles | |
gro.hasfulltext | No Full Text | |
gro.griffith.author | Loughlin, Wendy A. | |