Cyclofunctionalisation of epoxyalcohol derivatives. 1. Delivery of functionalised carbon for stereospecific synthesis of dihydrofurans and dihydroxyacids |
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| Authors: | Stuart W. McCombie Bandarpalle B. Shankar Ashit K. Ganguly |
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| Affiliation: | Anti-infectives Chemistry, Schering-Plough Corporation, 60 Orange Street, Bloomfield, N.J. 07003, U.S.A. |
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| 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 -CO2H or -CH2CO2H to C-2, with inversion. |
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