Total synthese of (±)-cyclolaurene, (±)-epicylolaurene and (±)-?-cuparenones
Data(s) |
1992
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Resumo |
The first total synthesis of (±)-cyclolaurene (Image ) and (±)-epicyclolaurene (Image ), and a new route to (±)-?-cuparenone (Image ) are reported. Thus, orthoester Claisen rearrangement of the cinnamyl alcohol Image furnished the eneester Image . Anhydrous CuSO, catalysed intramolecular cyclopropanation of the diazoketone derived from the ene-acid Image , generated a diastereoisomeric mixture of cyclopropyl ketone Image . The Huang-Minlon reduction of the ketones Image and Image furnished the cyclolaurene (Image ) and epicyclolaurene (Image ), whereas regiospecific ring cleavage using lithium in liquid ammonia furnished the ?-cuparenone (Image ). |
Formato |
application/pdf |
Identificador |
http://eprints.iisc.ernet.in/37968/1/Total_Syntheses_of.pdf Srikrishna, Adusumilli and Krishnan, Kathiresan (1992) Total synthese of (±)-cyclolaurene, (±)-epicylolaurene and (±)-?-cuparenones. In: Tetrahedron, 48 (16). pp. 3429-3436. |
Publicador |
Elsevier science |
Relação |
http://dx.doi.org/10.1016/0040-4020(92)85016-8 http://eprints.iisc.ernet.in/37968/ |
Palavras-Chave | #Organic Chemistry |
Tipo |
Journal Article PeerReviewed |