Tetrahedron Letters p. 8539 - 8542 (1993)
Update date:2022-08-11
Topics:
Craig
Craig, Donald
Pennington
Pennington, Mark W.
Warner
Warner, Peter
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 described.
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(1997)
