Total synthesis of (+)-gregatin B and E.
The first total synthesis of (+)-gregatin E and a new total synthesis of (+)-gregatin B are described. Key features of our synthetic approach involve a palladium-catalyzed cyclization-methoxycarbonylation of optically active propargylic acetate and a Suzuki-Miyaura coupling or CuTC-mediated coupling reaction. The absolute configuration of (+)-gregatin E (5R,5'S) is proposed.
Faculty of Pharmaceutical Sciences, Toho University , 2-2-1 Miyama, Funabashi, Chiba, 274-8510, Japan.
Taichi
T
Kusakabe
Yasuko
Y
Kawai
Keisuke
K
Kato
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010293:Pargyline / Q000031:analogs & derivatives / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D005663:Furans; C559559:gregatin B; C587470:gregatin E; D010165:Palladium; D010293:Pargyline