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A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) SNAr oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to… Click to show full abstract
A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) SNAr oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (–)-rotenone and (–)-deguelin, was prepared from d-araboascorbic acid in five steps. Also described is the conversion of (–)-deguelin into oxidized congeners, (–)-tephrosin and (+)-12a-epi-tephrosin.
Keywords:
synthetic approach;
stereospecific group;
cyclizations aryl;
approach rotenoids;
general synthetic;
group selective
Journal Title: Synthesis
Year Published: 2019
Link to full text (if available)
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Journal Title: Synthesis
Year Published: 2019
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!