Campus Units
Chemistry
Document Type
Article
Publication Version
Published Version
Publication Date
2014
Journal or Book Title
Organic Letters
Volume
16
Issue
12
First Page
3248
Last Page
3251
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.
Copyright Owner
American Chemical Society
Copyright Date
2014
Language
en
File Format
application/pdf
Recommended Citation
Abeykoon, Gayan A.; Chatterjee, Shreyosree; and Chen, Jason, "anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretense" (2014). Chemistry Publications. 890.
https://lib.dr.iastate.edu/chem_pubs/890
Comments
Reprinted (adapted) with permission from Org. Lett., 2014, 16 (12), pp 3248–3251. Copyright 2014 American Chemical Society.