anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretenseOrganic Letters
Publication VersionPublished Version
AbstractDifferentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.
Copyright OwnerAmerican Chemical Society
Citation InformationGayan A. Abeykoon, Shreyosree Chatterjee and Jason Chen. "anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretense" Organic Letters Vol. 16 Iss. 12 (2014) p. 3248 - 3251
Available at: http://works.bepress.com/jason-shih-hao-chen/2/