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Communication | Regular issue | Vol 16, No. 12, 1981, pp.2091-2104
Published online, 1st January, 1970
DOI: 10.3987/R-1981-12-2091
Total Synthesis of p-Menthenolides

Balkrishna S. Bal and Harold W. Pinnick*

*Department of Chemsitry, The University of Georgia, Athens, Georgia 30602, U.S.A.


A general approach to both cis- and trans-fused α-methylene γ-butyrolactones has been developed. This includes a new, mild method for the oxidation of α,β-unsaturated aldehydes. In addition, a new method to couple trans-α-methylene hydroxy acids into trans-lactones or, alternatively, cis-lactones has been developed. This strategy has been applied to the total synthesis of both cis- and trans-p-menthenolide, prepared in 35% (trans) and 21% (cis) overall yields from isopulegol.