Synthesis based on cyclohexadienes Part 36: an efficient methodology for the construction of spiro[4.5]decanes: a formal synthesis of acorone

Biju, John P and Pramod, K and Rao, Subba GSR (2003) Synthesis based on cyclohexadienes Part 36: an efficient methodology for the construction of spiro[4.5]decanes: a formal synthesis of acorone. In: ARKIVOC: Online Journal of Organic Chemistry (part 3). 88-103 .

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Abstract

An efficient strategy for the contruction of spiro[4.5] decanes is described and involves a bridgehead substitution of a methoxyl group by a methyl group followed by an oxidative cleavage of the tricyclo[5.2.2.0(1,5)] undecane 25 to produce the spiro[4.5] decanes 31 & 32 which are intermediates in the synthesis of acorone. A novel one-pot conversion of alpha-methoxy carboxylic acid to alpha-methyl carboxylic acid is described.

Item Type:	Journal Article
Publication:	ARKIVOC: Online Journal of Organic Chemistry
Publisher:	Arkat-USA, Inc
Additional Information:	Copyright of this article belongs to Arkat-USA, Inc.
Keywords:	Spiro[4.5]decane synthesis;bridgehead substitution;reductive alkylation
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	24 Aug 2011 06:04
Last Modified:	24 Aug 2011 06:04
URI:	http://eprints.iisc.ac.in/id/eprint/40250

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