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

Srikrishna, Adusumilli ; Krishnan, Kathiresan (1992) Total synthese of (±)-cyclolaurene, (±)-epicylolaurene and (±)-β-cuparenones Tetrahedron, 48 (16). pp. 3429-3436. ISSN 0040-4020

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The first total synthesis of (±)-cyclolaurene (1̲) and (±)-epicyclolaurene (5̲), and a new route to (±)-β-cuparenone (4̲) are reported. Thus, orthoester Claisen rearrangement of the cinnamyl alcohol 8̲ furnished the eneester 10̲. Anhydrous CuSO, catalysed intramolecular cyclopropanation of the diazoketone derived from the ene-acid 7̲, generated a diastereoisomeric mixture of cyclopropyl ketone 6̲. The Huang-Minlon reduction of the ketones 6a̲ and 6b̲ furnished the cyclolaurene (1̲) and epicyclolaurene (5̲), whereas regiospecific ring cleavage using lithium in liquid ammonia furnished the β-cuparenone (4̲).

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Cyclolaurenas; Cuparenoids; Orthoester Claisen Rearrangement; Diazoketone; Intramolecular Cyclopropanation
ID Code:48698
Deposited On:15 Jul 2011 11:27
Last Modified:15 Jul 2011 11:27

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