5 research outputs found
<i>anti</i>-Diols from α‑Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from <i>Dracontium loretense</i>
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 <i>anti</i> 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 <i>Dracontium
loretense</i> with incomplete stereochemical assignments. Spectroscopic
comparisons between the synthetic and natural oxylipins led to unambiguous
assignments