Racemic guaiol [guai-1(5)-en-11-ol] has been synthesised from laevulinic acid and 2-methylcyclopentanone via 1-methyltricyclo[6.2.1.02,6]undec-2(6)-ene-5,11-dione. Bridge fission of this intermediate yielded an octahydroazulene keto-ester which has been elaborated to guaiol.
Geo. L. Buchanan and G. A. R. Young, J. Chem. Soc., Perkin Trans. 1, 1973, 2404 DOI: 10.1039/P19730002404
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