Novel Synthesis of Right Segment of Solanoeclepin A

Novel Synthesis of Right Segment of Solanoeclepin A

The highly strained tricyclo­[5.2.1.01,6]­decene skeleton of solanoeclepin A was synthesized through two key C–C bond forming processes; thus, a Hg(TFA)2-mediated oxymercuration followed an intramolecular aldol reaction to B and a SmI2-mediated cyclization of C between an aldehyde and an unsaturated...

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Veröffentlicht in:Organic letters 2014-08, Vol.16 (16), p.4166-4169
Hauptverfasser: Chuang, Hsiang-Yu, Isobe, Minoru
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Bridged-Ring Compounds - chemical synthesis
Bridged-Ring Compounds - chemistry
Cyclization
Cyclobutanes - chemistry
Hexanes - chemical synthesis
Hexanes - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:The highly strained tricyclo­[5.2.1.01,6]­decene skeleton of solanoeclepin A was synthesized through two key C–C bond forming processes; thus, a Hg(TFA)2-mediated oxymercuration followed an intramolecular aldol reaction to B and a SmI2-mediated cyclization of C between an aldehyde and an unsaturated ester to form the cyclobutane D having a tricyclo­[5.2.1.01,6]­dodecene.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501858w