A novel and concise synthesis of spirodienone alkaloids using hypervalent iodine(III) reagents.
Intramolecular oxidative coupling reaction of N-protected benzyltetrahydroisoquinoline derivatives using hypervalent iodine(III) reagents was investigated. The use of remarkable combination of phenyliodine bis (trifluoroacetate) (PIFA) and heteropoly acid (HPA) in wet acetonitrile smoothly afforded morphinandienone alkaloids, while neospirinedienone alkaloids were obtained in high yield under anhydrous conditions.
Graduate School of Pharmaceutical Sciences, Osaka University, Osaka, Japan.
Hiromi
H
Hamamoto
Yukiko
Y
Shiozaki
Kayoko
K
Hata
Hirofumi
H
Tohma
Yasuyuki
Y
Kita
D000097:Acetonitriles; D000470:Alkaloids / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis*; D044005:Tetrahydroisoquinolines / Q000737:chemistry*
D000097:Acetonitriles; D000470:Alkaloids; D007202:Indicators and Reagents; D009019:Morphinans; D013141:Spiro Compounds; D044005:Tetrahydroisoquinolines; C032159:acetonitrile