Synthesis of the new furo[3,2-h]isoquinoline alkaloid, TMC-120B from Aspergillus ustus.
A total synthesis of a new furo[3,2-h]isoquinoline alkaloid TMC120-B (2), isolated from Aspergillus ustus together with two related compounds, has been completed in sixteen steps. The key step is the synthesis of the appropriate 3,7,8-trisubstituted isoquinoline framework (23) based on a thermal electrocyclic reaction of the 1-aza 6pi-electron system involving the benzene double bond. In addition, the microwave assisted electrocyclic reaction of this system was newly performed.
Kumemura
Teppei
T
Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Hiroshima.
Choshi
Tominari
T
Hirata
Aki
A
Sera
Mitsuko
M
Takahashi
Yohhei
Y
Nobuhiro
Junko
J
Hibino
Satoshi
S
D001230:Aspergillus / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis*; D004563:Electrochemistry; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D013055:Spectrophotometry, Infrared
D001572:Benzofurans; D007202:Indicators and Reagents; D007546:Isoquinolines; C402697:TMC 120B