Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 48, Pages 17714-17718Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja907931u
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- NIH [GM57014]
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A unified approach to the pyrrolidine triacid natural products isodomoic acids G and H has been developed. Total syntheses of both natural products were completed, and determination of the correct stereostructure of isodomoic acid G was established by comparing 5'-(R) and 5'-(S) isomers to a sample of authentic material. A nickel-catalyzed cyclization constructs the pyrrolidine ring while simultaneously establishing either the E or Z stereochemistry of an exocyclic tetrasubstituted alkene. Stereoselective assembly of both the E- and Z-alkenes,of the natural products is made possible by a predictable strategy that alters the timing of substituent introduction to control alkene stereochemistry.
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