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

Pure and Applied Chemistry

Vol. 73, Issue 2

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.

* Lecture presented at the XIXth International Conference on Organometallic Chemistry (XIX ICOMC) , Shanghai, China, 23-28 July 2000. Other presentations are published in this issue, pp. 205-376.
** Corresponding author

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