Tetrahedron Letters p. 8989 - 8992 (1999)
Update date:2022-07-29
Topics:
Khan, Noshena
Bastola, Shyamal R.
Witter, Kevin G.
Scheiner, Peter
L-homolamivudine (2a, (2R,5R)-(+)-cis-5-(1-cytosinylmethyl)-2-hydroxymethyl-1,3-oxathiolane) and its 5-fluoro congener (2b, L-homoFTC) have been prepared from (R)-glycidol by diastereoselective synthesis. Enantioselectivity resulted from stereoselective cyclothioacetalization that preferentially gave the (2R,5R)-cis-2,5-disubstituted-1,3-oxathiolane (5), cis/trans = 5.7.
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