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Article
anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretense
Organic Letters
  • Gayan A. Abeykoon, Iowa State University
  • Shreyosree Chatterjee, Iowa State University
  • Jason Chen, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
1-1-2014
DOI
10.1021/ol501263y
Abstract
Differentially 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.
Comments

Reprinted (adapted) with permission from Org. Lett., 2014, 16 (12), pp 3248–3251. Copyright 2014 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Gayan 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/