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Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of $(\pm)$-Acorone and Isoacorones

Srikrishna, A and Kumar, Praveen P (2000) Claisen Rearrangement Based Methodology for the Spiroannulation of a Cyclopentane Ring. Formal Total Synthesis of $(\pm)$-Acorone and Isoacorones. In: Tetrahedron, 56 (41). pp. 8189-8195.

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Abstract

A Claisen rearrangement based methodology for spiroannulation of a cyclopentane ring to cyclic precursors and its application in the formal total synthesis of acorones 1 is described. Thus, Claisen rearrangement of 2-cycloalkylideneethanols 12 with 2-methoxypropene and a catalytic amount of mercuric acetate generates 4,4-substituted hex-5-en-2-ones 13. Ozonolytic cleavage of the terminal olefin in the enones 13 and intramolecular aldol condensation of the resulting keto-aldehydes 14 furnishes the spiroannulated compounds 15.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 09 Oct 2007
Last Modified: 19 Sep 2010 04:40
URI: http://eprints.iisc.ernet.in/id/eprint/12168

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