Journal
ORGANIC LETTERS
Volume 14, Issue 6, Pages 1648-1651Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol300432y
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- Natural Sciences and Engineering Research Council (Canada)
- University of Saskatchewan
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Enantioselective synthesis of the enantiomer of caloundrin B was achieved by strategic aldol coupling of an enantiopure trioxaadamantane-containing ketone with a racemic pyrone-containing aldehyde via kinetic resolution. In the presence of imidazole, ent-caloundrin B is cleanly isomerized to ent-siphonarin B confirming the proposed structure and absolute configuration for caloundrin B and establishing that it is a plausible biosynthetic product from which siphonarin B and baconipyrones A and C can originate.
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