Anwendung der α‐Alkinon‐Cyclisierung: Totalsynthese von (±)‐Alben

Application of the α‐Alkynone Cyclization: Total Synthesis of (±)‐Albene A synthesis of the racemic form of the natural tricyclic hydrocarbon albene (1) from the Diels‐Alder adduct 2 of tiglyl chloride and cyclopentadiene is described (24% yield). The key step 5→6 involves a thermal α‐alkynone cycli...

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Veröffentlicht in:Helvetica chimica acta 1983-03, Vol.66 (2), p.627-632
Hauptverfasser: Manzardo, Giuseppe G. G., Karpf, Martin, Dreiding, André S.
Format: Artikel
Sprache:eng
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Zusammenfassung:Application of the α‐Alkynone Cyclization: Total Synthesis of (±)‐Albene A synthesis of the racemic form of the natural tricyclic hydrocarbon albene (1) from the Diels‐Alder adduct 2 of tiglyl chloride and cyclopentadiene is described (24% yield). The key step 5→6 involves a thermal α‐alkynone cyclization (Scheme 3), which is able to establish a new quarternary C‐atom at an unactivated position with a high degree of regiospecificity.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19830660224