Ethoxycarbonylmethylenetriphenylphosphorane in Carbohydrate Chemistry, Part III:§  A Short and Highly Efficient Synthesis of (-)-Epigoniofufurone

K. R. C. Prakash; S. Prahlada Rao

doi:10.1055/s-1993-22371

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Synlett 1993; 1993(2): 123-124
DOI: 10.1055/s-1993-22371

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Ethoxycarbonylmethylenetriphenylphosphorane in Carbohydrate Chemistry, Part III:§ A Short and Highly Efficient Synthesis of (-)-Epigoniofufurone

K. R. C. Prakash^* , S. Prahlada Rao

^*Bio-Organic Laboratory, Indian Institute of Chemical Technology, Hyderabad 500007, India

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Publication Date:
19 March 2002 (online)

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(-)-Epigoniofufurone is synthesised in a very efficient way from diacetone glucose in 6 steps in 30% overall yield. The highlight of our synthesis is a fortuitous one-pot elaboration of 2-deoxy-3,6-anhydro-1,4-glyconolactone skeleton present in the natural product by a bis-cyclisation process accompanying the Wittig reaction of 2-hydroxy free lactol with the title ylide.