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Total synthese of (±)-cyclolaurene, (±)-epicylolaurene and (±)-?-cuparenones

Srikrishna, Adusumilli and Krishnan, Kathiresan (1992) Total synthese of (±)-cyclolaurene, (±)-epicylolaurene and (±)-?-cuparenones. In: Tetrahedron, 48 (16). pp. 3429-3436.

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Official URL: http://dx.doi.org/10.1016/0040-4020(92)85016-8


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 ).

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier science
Additional Information: Copyright of this article belongs to Elsevier science.
Keywords: Cyclolaurenas;cuparenoids;orthoester Claisen rearrangement; diazoketone;intramolecular cyclopropanation.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 30 May 2011 05:14
Last Modified: 30 May 2011 05:14
URI: http://eprints.iisc.ac.in/id/eprint/37968

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