Facile and efficient total synthesis of (+)-preussin.
[structure] The enantioselective total synthesis of (+)-preussin, a potent antifungal agent, has been achieved. The key steps are a Pd(0)-catalyzed oxazoline-forming reaction from L-phenylalanine, hydrogenolysis, and subsequent diastereoselective reductive cyclization of the intermediate aminoketone to pyrrolidine using Pearlman's catalyst.
Lee
K Y
KY
College of Pharmacy, SungKyunKwan University, Suwon 440-746, Korea.
Kim
Y H
YH
Oh
C Y
CY
Ham
W H
WH
D000841:Anisomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000935:Antifungal Agents / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D006865:Hydrogenation; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium; D010649:Phenylalanine / Q000737:chemistry; D013237:Stereoisomerism
D000935:Antifungal Agents; D010080:Oxazoles; C058280:preussin; D010649:Phenylalanine; D010165:Palladium; D000841:Anisomycin