Diastereoselective synthesis of the indeno-tetrahydropyridine core bearing a diaryl-substituted stereogenic quaternary carbon center of haouamine B.
The characteristic indeno-tetrahydropyridine core of cytotoxic haouamine B (2) was efficiently synthesized featuring the diastereoselective construction of a diaryl-substituted stereogenic quaternary center by an intramolecular Pd-catalyzed α-C-arylation and subsequent direct conversion of the vinylogous imide function into the C2-C25 double bond by TsNHNH(2).
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan.
Takeshi
T
Tanaka
Hiromi
H
Inui
Hiroshi
H
Kida
Takeshi
T
Kodama
Takuya
T
Okamoto
Aki
A
Takeshima
Yoshimitsu
Y
Tachi
Yoshiki
Y
Morimoto
D002384:Catalysis; D003603:Cytotoxins / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D000097566:Cyclophanes
D003603:Cytotoxins; D006576:Heterocyclic Compounds, 4 or More Rings; D007192:Indenes; D011725:Pyridines; C474768:haouamine B; D000097566:Cyclophanes; C512228:indeno-tetrahydropyridine