Total syntheses of isodomoic acids G and H: an exercise in tetrasubstituted alkene synthesis.
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.
Ni
Yike
Y
Department of Chemistry, 930 North University Avenue, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Kassab
Refaie M
RM
Chevliakov
Maxim V
MV
Montgomery
John
J
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D006538:Heptanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D001688:Biological Products; D006538:Heptanoic Acids; C547165:isodomoic acid G; C547164:isodomoic acid H