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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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[220.127.116.11(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|
|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|
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