Diastereoselective Additions of Allylmetal Reagents to Free and Protectedsyn-?,?-Dihydroxyketones Enable Efficient Synthetic Routes to Methyl Trioxacarcinoside A

Authors :: Smaltz, Daniel Jonathan
Svenda, Jakub
Myers, Andrew G.
Source :: Quick submit: 2014-02-27T22:10:22-05:00, Smaltz, 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.
Publication Year :: 2012
Publisher :: American Chemical Society (ACS), 2012.
Abstract: Two 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.<br />Chemistry and Chemical Biology

Language :: English
ISSN :: 15237060
Database :: Digital Access to Scholarship at Harvard (DASH)
Journal :: Quick submit: 2014-02-27T22:10:22-05:00, Smaltz, 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.
Publication Type :: Academic Journal
Accession number :: edshld.1.33724105
Document Type :: Journal Article
Full Text :: https://doi.org/10.1021/ol300377a

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