Total syntheses of all stereoisomers of phenatic acid B.
The total syntheses of all stereoisomers of phenatic acid B and determination of their absolute configuration are described. The synthetic strategy is based on an efficient combination of the Sharpless asymmetric dihydroxylation, the Johnson-Claisen rearrangement, and hydroboration-oxidation. It involves 11-12 steps and overall yield of 5-8%.
Department of Chemistry, Indian Institute of Technology Bombay, Powai 400076 Mumbai, Maharashtra India. rfernand@chem.iitb.ac.in
Rodney A
RA
Fernandes
Asim K
AK
Chowdhury
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000085:Acetates; D010636:Phenols; C502102:phenatic acid B