Tetrahedron letters

Stereoselective template-directed C-glycosidation. Synthesis of 5-membered oxygen heterocycles via cation-mediated intramolecular cyclization reactions

D Craig, MW Pennington, P Warner

Index: Craig; Craig, Donald; Pennington; Pennington, Mark W.; Warner; Warner, Peter Tetrahedron Letters, 1993 , vol. 34, # 52 p. 8539 - 8542

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Citation Number: 12

Abstract

Abstract Construction of 5-membered oxygen heterocycles by intramolecular template- directed C-glycosidation is described. Alkylation of thioglycoside 5 with enone 6 followed by enol etherification gave cyclization substrates 8. Compound 8a underwent silver (I) trifluoromethanesulfonate-mediated ring-closure to give a 1.7: 1 mixture of 9α and 9β; isomer 8s gave an 8.5: 1 ratio. Some derivatization reactions of the bicyclic products are ...