Issue 0, 1973

A new stereoselective synthesis of trans-chrysanthemic acid [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid]

Abstract

Base-catalysed interaction of 3-chloro-3-methylbut-1-yne and 3-methylbut-2-en-1 -ol has been shown to produce 2,2-dimethyl-3-(2-methylprop-1-enylidene)cyclopropylmethanol (2). Selective reduction of this allene and subsequent oxidation gave racemic trans-chrysanthemic acid. The method represents a versatile route to many analogues.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 133-137

A new stereoselective synthesis of trans-chrysanthemic acid [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid]

R. W. Mills, R. D. H. Murray and R. A. Raphael, J. Chem. Soc., Perkin Trans. 1, 1973, 133 DOI: 10.1039/P19730000133

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