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- W2000334746 abstract "Stereospecific syntheses of 6 (I, II, XVI, XXV, XXVI and XXXII) out fo 8 of the possible iridolactones are described. The lactone IV, produced by lactonization of trans -pulegenic acid (III), was converted by LAH reduction and acetylation to 3-(α-hydroxyisopropyl)-2-acetoxymethyl-1-methylcyclopentane ( cis-trans -V). Dehydration of V with refluxing acetic anhydride gave 2-acetoxy-methyl-3-isopropenyl-1-methylcyclopentane ( cis-trans -VII). Hydroboration of VII followed by oxidation and hydrolysis gave (−)-iridomyrmecin (I) which was epimerized with sodium methoxide to (+)-isoiridomyrmecin (II). The cis-cis -iridolactones XXV and XXVI were produced in similar fashiong from the cis-cis -lactone XVII. Treatment of the lactones IV and XVII with hydrogen chloride in methanol gave methyl trans-trans and trans-cis -chloropulegenates X and XXVII, respectively. These esters were then transformed into iridolactones XVI and XXXII. The biosynthesis of iridomyrmecin is discussed." @default.
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- W2000334746 date "1965-01-01" @default.
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- W2000334746 title "Stereospecific synthesis of iridomyrmecin and related iridolactones" @default.
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- W2000334746 doi "https://doi.org/10.1016/0040-4020(65)80066-7" @default.
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