Toward the synthesis of cobyric acid. Enantioselective syntheses of completely differentiated ring D synthons.
Alkyne acids 11 were prepared in an enantioselective fashion from allylic ester derivatives 18 or 20 by Ireland-Claisen rearrangement, followed by Si-assisted elimination of HBr. The title compounds are attractive ring D synthons for an ongoing synthesis of cobyric acid.
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
Hui
H
Wang
Carlos
C
Tassa
Peter A
PA
Jacobi
D000143:Acids / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry; D013237:Stereoisomerism; D014805:Vitamin B 12 / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000143:Acids; D011758:Pyrroles; C012851:cobyric acid; C013231:pyrroline; D014805:Vitamin B 12