| Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork-Danheiser approach: preparation of mono-, bi-, and tricyclic systems. | |
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MedLine Citation:
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PMID: 22009489 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A general method for the synthesis of β-substituted and unsubstituted cycloheptenones bearing enantioenriched all-carbon γ-quaternary stereocenters is reported. Hydride or organometallic addition to a seven-membered ring vinylogous ester followed by finely tuned quenching parameters achieves elimination to the corresponding cycloheptenone. The resulting enones are elaborated to bi- and tricyclic compounds with potential for the preparation of non-natural analogs and whose structures are embedded in a number of cycloheptanoid natural products. |
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Authors:
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Nathan B Bennett; Allen Y Hong; Andrew M Harned; Brian M Stoltz |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't Date: 2011-10-19 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 10 ISSN: 1477-0539 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2012 Jan |
Date Detail:
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Created Date: 2011-12-05 Completed Date: 2012-03-19 Revised Date: 2013-04-12 |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 56-9 Citation Subset: IM |
Affiliation:
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The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, California Institute of Technology, Division of Chemistry and Chemical Engineering, Mail Code 101-20, Pasadena, CA 91125, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkylation Heptanes / chemistry* Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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R01 GM080269/GM/NIGMS NIH HHS; R01 GM080269-06/GM/NIGMS NIH HHS; R01GM080269-01/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Heptanes |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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