On the Origin of Siphonariid Polypropionates: Total Synthesis of Caloundrin B and Its Isomerization to Siphonarin B

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-sip...

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Bibliographic Details
Published in:Organic letters 2012-03, Vol.14 (6), p.1648-1651
Main Authors: Becerril-Jiménez, Fabiola, Ward, Dale E
Format: Article
Language:English
Subjects:
Adamantane - analogs & derivatives
Adamantane - chemical synthesis
Adamantane - chemistry
Aldehydes - chemistry
Animals
Biological Products
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Mollusca - chemistry
Pyrones - chemical synthesis
Pyrones - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300432y