Ring-construction/stereoselective functionalization cascade: total synthesis of pachastrissamine (jaspine B) through palladium-catalyzed bis-cyclization of propargyl chlorides and carbonates.
Palladium(0)-catalyzed cyclization of bromoallenes, propargyl chlorides, and carbonates bearing hydroxy and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. Cyclization reactivity is dependent on the relative configuration of the benzamide and leaving groups, and on the nature of the leaving groups. This bis-cyclization was used as the key step in a short total synthesis of pachastrissamine, which is a biologically active marine natural product.
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
D000480:Alkynes / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D003500:Cyclization; D010165:Palladium / Q000737:chemistry; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
D000480:Alkynes; D002254:Carbonates; D002712:Chlorides; C468594:pachastrissamine; D010165:Palladium; D013110:Sphingosine