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Pure Appl. Chem., 2001, Vol. 73, No. 2, pp. 265-269

Synthesis of oxygen heterocycles via alkynyltungsten compounds

Rai-Shung Liu

Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan ROC

Abstract: This short review article covers some useful applications of alkynyltungsten compounds to the syntheses of complex lactones. Two types of cyclizations will be emphasized: (1) cycloalkenylation of tungsten-alkynol compounds with aldehydes to give a-alkylidene oxacarbeniums, further leading to a-alkylidene lactones and (2) intramolecular [3+2]-cycloaddition of epoxides to give bicyclic lactones. The new methodologies can provide a short synthesis of enantiopure lactones such as (-) -epilitsenolide C2, (+) -listenolide C1, (+) -isodihydromahubanolide A, (+) -blastmycinone, and (-) -epi-blastmycinone.