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Mintlactone 1 and (+)-isomintlactone 2 are endo R,β-unsaturated monoterpene-γ-lactones, isolated for the first time in 1968 from Mentha cardiaca. 1 These two diastereomeric p-menthanolides are also found in Mentha arvensis, 2 and as minor constituents of the commercially important essential oil (peppermint oil) of Mentha piperita L. 3

This review summarizes the papers dealing with the synthesis of mintlactone and isomintlactone, two natural monoterpenic lactones found in mint oils.

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Reaction of β,γ-UnsaturatedCarboxylic Acids with Thallium Triacetate (TTA): Lactonization vs Oxidative Decarboxylation. -The reaction of β,γ-unsaturated carboxylic acids (I), (III), and (VIII) with thallium triacetate gives lactones [cf. (II), (V)] and/or decarboxylated products [cf. (VI), (VII), (IX), (X)] in ratios depending on the substitution pattern of the substrates. A free-radical chain mechanism for the oxidative decarboxylation pathway is proposed. -(FERRAZ, HELENA M. C.; GRAZINI, MONICA V. A.; SILVA JR., LUIZ F.; LONGO JR., LUIZ S.; Synth. Commun. 29 (1999Commun. 29 ( ) 11, 1953Commun. 29 ( -1964 Inst. Quim., Univ. Sao Paulo, 05599 Sao Paulo, Brazil; EN)