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Spiroannulation of a cyclopentane ring. Synthesis of spiro[4.n](n+5)alk-2-en-1-ones

Srikrishna, A and Kumar, PP (1999) Spiroannulation of a cyclopentane ring. Synthesis of spiro[4.n](n+5)alk-2-en-1-ones. In: Journal of the Indian Chemical Society, 76 (11-12). pp. 521-526.

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A methodology based on Claisen rearrangement-Wacker oxidation and intramolecular aldol condensation strategy starting from cyclic ketones leading to spiro[4.n](n+5)alk-2-en-1-ones has been developed. Thus one-pot Claisen rearrangement of the alkyl alcohols 6a-c furnished the aldehydes 8a-c, which on regiospecific oxidation using Wacker conditions generated the keto-aldehydes 9a-c. Finally, intramolecular aldol condensation transformed the keto-aldehydes 9a-c into spiroannulated products 10a-c.

Item Type: Journal Article
Publication: Journal of the Indian Chemical Society
Publisher: Indian Chemical Society
Additional Information: Copyright of this article belongs to Indian Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 29 Jun 2011 08:39
Last Modified: 29 Jun 2011 08:39
URI: http://eprints.iisc.ac.in/id/eprint/38778

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