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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Abstract

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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