Issue 0, 1973

Studies on terpenes. Part II. Elaboration of 9-methyl-6-p-tolyl-7-oxatricyclo[4,3,0,03,9]nonane into (+)-(1R,3S)-3-isopropenyl-1-p-tolylcyclopentane-1-carboxylic acid, a model for sesquiterpene synthesis

Abstract

The non-enolisable ketone 3-methyl-2-oxo-1-p-tolylnorbornan-3α-ylmethyl toluene-p-sulphonate (IX) undergoes fragmentation on treatment with base to the title cyclopentanecarboxylic acid derivative (XI), a model for the synthesis of spiro[4,5]decane sesquiterpenes [(IV)–(VII)].

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 76-78

Studies on terpenes. Part II. Elaboration of 9-methyl-6-p-tolyl-7-oxatricyclo[4,3,0,03,9]nonane into (+)-(1R,3S)-3-isopropenyl-1-p-tolylcyclopentane-1-carboxylic acid, a model for sesquiterpene synthesis

N. Bosworth and P. D. Magnus, J. Chem. Soc., Perkin Trans. 1, 1973, 76 DOI: 10.1039/P19730000076

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