Synthesis of tri-O-acetyl-D-allal from levoglucosenone.

Org Lett

Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, CONICET Suipacha 531, S2002LRK Rosario, Argentina.

Published: September 2012

Tri-O-acetyl-D-allal has been enantiospecifically synthesized in six steps from levoglucosenone in 55% overall yield. A key step in the synthesis is the anhydro bridge ring-opening with concomitant formation of a 1,3-oxathiolane-2-thione ring.

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Source
http://dx.doi.org/10.1021/ol302061aDOI Listing

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