Journal
ORGANIC LETTERS
Volume 16, Issue 12, Pages 3248-3251Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol501263y
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Funding
- Iowa State University
- National Science Foundation [CHE 0946687, MRI 1040098]
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Differentially protected 1,2-diols were synthesized by enantioselective aldehyde alpha-oxygenation followed by organo-magnesium 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.
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