Asymmetric synthesis of the balanol heterocycle via a palladium-mediated epimerization and olefin metathesis.
[formula: see text] The enantioselective formal synthesis of balanol, a potent protein kinase C inhibitor, was accomplished from D-serine utilizing a Pd-catalyzed equilibration of diastereomeric 5-vinyloxazolines to set the stereochemistry of the vicinal amino and hydroxyl groups. A ruthenium-catalyzed ring-closing metathesis was employed to form the seven-membered nitrogen heterocyle.
Cook
G R
GR
Department of Chemistry, North Dakota State University, Fargo 58105-5516, USA. grcook@plains.nodak.edu
Shanker
P S
PS
Peterson
S L
SL
D000475:Alkenes / Q000737:chemistry*; D001381:Azepines / Q000138:chemical synthesis*; D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D062385:Hydroxybenzoates / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*; D012428:Ruthenium; D013237:Stereoisomerism
D000475:Alkenes; D001381:Azepines; D004791:Enzyme Inhibitors; D062385:Hydroxybenzoates; D010165:Palladium; C015405:ophiocordin; D012428:Ruthenium; D011493:Protein Kinase C