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The total synthesis of the water mold sex hormone oogoniol
dc.contributor.authorMase, Toshiakien_US
dc.contributor.authorIchita, Junjien_US
dc.contributor.authorMarino, Joseph P.en_US
dc.contributor.authorKoreeda, Masatoen_US
dc.date.accessioned2006-04-07T21:00:59Z
dc.date.available2006-04-07T21:00:59Z
dc.date.issued1989en_US
dc.identifier.citationMase, Toshiaki, Ichita, Junji, Marino, Joseph P., Koreeda, Masato (1989)."The total synthesis of the water mold sex hormone oogoniol." Tetrahedron Letters 30(16): 2075-2078. <http://hdl.handle.net/2027.42/28249>en_US
dc.identifier.urihttp://www.sciencedirect.com/science/article/B6THS-42HFTDT-1F/2/a49771279246939ebe31d9eb88bcd60cen_US
dc.identifier.urihttps://hdl.handle.net/2027.42/28249
dc.description.abstractThe water mold sex hormone oogoniol (1a) has been synthesized from adrenosterone in 18 steps in 7.0% overall yield. The crucial step introduces the stereochemistry at C-15 and C-20 through a highly efficient 1,4-addition of the organocyanocuprate generated from the side chain Grignard reagent (4) and CuCN to the steroidal 15[beta],16[beta]-epoxy-17(20) (E)-ethylidene 2.en_US
dc.format.extent261854 bytes
dc.format.extent3118 bytes
dc.format.mimetypeapplication/pdf
dc.format.mimetypetext/plain
dc.language.isoen_US
dc.publisherElsevieren_US
dc.titleThe total synthesis of the water mold sex hormone oogoniolen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelMaterials Science and Engineeringen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbsecondlevelChemical Engineeringen_US
dc.subject.hlbsecondlevelBiological Chemistryen_US
dc.subject.hlbtoplevelEngineeringen_US
dc.subject.hlbtoplevelScienceen_US
dc.subject.hlbtoplevelHealth Sciencesen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan Ann Arbor, Michigan 48109, USAen_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan Ann Arbor, Michigan 48109, USAen_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan Ann Arbor, Michigan 48109, USAen_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan Ann Arbor, Michigan 48109, USAen_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/28249/1/0000702.pdfen_US
dc.identifier.doihttp://dx.doi.org/10.1016/S0040-4039(01)93715-3en_US
dc.identifier.sourceTetrahedron Lettersen_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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