Ring-construction/stereoselective functionalization cascade: total synthesis of pachastrissamine (jaspine B) through palladium-catalyzed bis-cyclization of bromoallenes.
Palladium(0)-catalyzed cyclization of bromoallenes bearing hydroxyl and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. With this bis-cyclization as the key step, a short total synthesis of pachastrissamine, a biologically active marine natural product, was achieved.
Inuki
Shinsuke
S
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Yoshimitsu
Yuji
Y
Oishi
Shinya
S
Fujii
Nobutaka
N
Ohno
Hiroaki
H
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; C468594:pachastrissamine; D010165:Palladium; D013110:Sphingosine