Vinigrol : a compact, Diene-Transmissive Diels-Alder strategy to the tricyclic core

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DOIResolve DOI: http://doi.org/10.1021/ol702202b
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TypeArticle
Journal titleOrganic Letters
ISSN1523-7060
Volume9
Issue25
Pages51635166; # of pages: 4
AbstractA short (six steps from 17), versatile route to the tricyclic core of Vinigrol is described. A Lewis acid catalyzed and self-assembled Diels-Alder (LACASA-DA) reaction from the homoallylic cross-conjugated trienol 15 with N-methylmaleimide afforded the monoadduct 17 with diastereo-, regio-, and chemoselective control. Oxidation and installation of an acetylene (Ohira's reagent) followed by further manipulations afforded trienone 24. The second intramolecular Diels-Alder (at 45 C) reaction assembled the tricyclic skeleton 25 directly. The configuration of 25 was confirmed by X-ray analysis.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier18697458
NPARC number12339323
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Record identifier06232f7a-0d77-4555-9a7d-a812e8ad725d
Record created2009-09-11
Record modified2016-05-09
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