Smaltz, Daniel JonathanSvenda, JakubMyers, Andrew2017-08-082012Smaltz, Daniel J., Jakub Švenda, and Andrew G. Myers. 2012. “Diastereoselective Additions of Allylmetal Reagents to Free and Protectedsyn-?,?-Dihydroxyketones Enable Efficient Synthetic Routes to Methyl Trioxacarcinoside A.” Organic Letters 14 (7) (April 6): 1812–1815. doi:10.1021/ol300377a.1523-7060http://nrs.harvard.edu/urn-3:HUL.InstRepos:33724105Two routes to the 2,6-dideoxysugar methyl trioxacarcinoside A are described. Each was enabled by an apparent α-chelation-controlled addition of an allylmetal reagent to a ketone substrate containing a free α-hydroxyl group and a β-hydroxyl substituent, either free or protected as the corresponding di-tert-butylmethyl silyl ether. Both routes provide practical access to gram-quantities of trioxacarcinose A in a form suitable for glycosidic coupling reactions.en-USJournal Article2014-02-28Andrew Myers10.1021/ol300377a