Issue 5, 1994

Use of diazophosphonates in the synthesis of cyclic ethers. Part 2. Synthesis of the pyranooxepane and oxepanooxepane subunits of marine polyether toxins

Abstract

3-Oxooxepan-2-ylphosphonates 3, prepared by rhodium carbenoid cyclisation of the diazophosphonates 1, are readily elaborated into the keto alcohols 6, by Wadsworth–Emmons reaction, hydrogenation and epimerisation. Cyclisation of 6 using trimethylsilyl triflate–triethylsilane results in formation of 7–6- and 7–7-bicyclic ethers 10, with trans selectivity.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 501-506

Use of diazophosphonates in the synthesis of cyclic ethers. Part 2. Synthesis of the pyranooxepane and oxepanooxepane subunits of marine polyether toxins

C. J. Moody, E. H. B. Sie and J. J. Kulagowski, J. Chem. Soc., Perkin Trans. 1, 1994, 501 DOI: 10.1039/P19940000501

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