Tetrahedron letters

Cyclofunctionalisation of epoxyalcohol derivatives. 1. Delivery of functionalised carbon for stereospecific synthesis of dihydrofurans and dihydroxyacids

SW McCombie, BB Shankar, AK Ganguly

Index: McCombie, Stuart W.; Shankar, Bandarpalle B.; Ganguly, Ashit K. Tetrahedron Letters, 1985 , vol. 26, # 51 p. 6301 - 6304

Full Text: HTML

Citation Number: 23

Abstract

Abstract E-2-(Phenylsulfonyl) vinyl ethers of 2, 3-epoxyalcohols are stereospecifically rearranged to 3-(phenylsulfony])-4-(1-hydroxyalkyl)-4, 5-dihydrofurans on treatment with LDA. Oxidation of these compounds or the derived des-sulfonyl compounds provides esters or lactones which correspond to regiospecific delivery of-CO 2 H or-CH 2 CO 2 H to C-2, with inversion.