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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
16
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pubmed:dateCreated |
2004-4-21
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pubmed:abstractText |
An efficient asymmetric synthesis of a selective estrogen receptor modulator (SERM) that has a dihydrobenzoxathiin core structure bearing two stereogenic centers is reported. The stereogenic centers were established by an unprecedented chiral sulfoxide-directed stereospecific reduction of an alpha,beta-unsaturated sulfoxide to the saturated sulfide in one step. Studies to elucidate the mechanism for this reduction are reported. Highly efficient Cu(I)-mediated ether formation was used to install the ether side chain, and selective debenzylation conditions were developed to remove the benzyl protecting groups on the phenols.
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pubmed:commentsCorrections |
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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|
pubmed:chemical |
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|
pubmed:status |
MEDLINE
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pubmed:month |
Apr
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pubmed:issn |
0027-8424
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pubmed:author |
pubmed-author:BioMatthewM,
pubmed-author:ChilenskiJennifer RJR,
pubmed-author:JavadiGaryG,
pubmed-author:KassimAmudeA,
pubmed-author:KingAnthony OAO,
pubmed-author:LangFengruiF,
pubmed-author:LeazerJohnnie LJLJr,
pubmed-author:MathreDavid JDJ,
pubmed-author:ReamerRobert ARA,
pubmed-author:RosnerThorstenT,
pubmed-author:SongZhiguo JZJ,
pubmed-author:TillyerRichardR,
pubmed-author:TschaenDavid MDM,
pubmed-author:VolanteR PRP,
pubmed-author:WatersMarjorie SMS,
pubmed-author:ZewgeDanielD
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pubmed:issnType |
Print
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|
pubmed:day |
20
|
|
pubmed:volume |
101
|
|
pubmed:owner |
NLM
|
|
pubmed:authorsComplete |
Y
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pubmed:pagination |
5776-81
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pubmed:dateRevised |
2010-9-20
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pubmed:meshHeading |
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pubmed:year |
2004
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pubmed:articleTitle |
An efficient asymmetric synthesis of an estrogen receptor modulator by sulfoxide-directed borane reduction.
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pubmed:affiliation |
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, NJ 07065, USA. zhiguo_song@merck.com
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pubmed:publicationType |
Journal Article
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