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.
Hamamoto
Hiromi
H
Graduate School of Pharmaceutical Sciences, Osaka University, Osaka, Japan.
Shiozaki
Yukiko
Y
Hata
Kayoko
K
Tohma
Hirofumi
H
Kita
Yasuyuki
Y
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