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 |
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Publication: | Tetrahedron |
Publisher: | Elsevier |
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.ac.in/id/eprint/12168 |
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