Total synthesis and absolute configuration of (-)-berkeleyamide A.
A chiral-pool approach to (-)-berkeleyamide A 1 based on a diastereoselective nitrile oxide [3 + 2]-cycloaddition completes the first total synthesis establishing the absolute stereochemistry of the natural product.
Sperry
Jonathan
J
Department of Chemistry, University of Auckland, 23 Symonds Street, Auckland, New Zealand.
Harris
Eric B J
EB
Brimble
Margaret A
MA
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D001688:Biological Products; D011760:Pyrrolidinones; C547261:berkeleyamide A