Total Synthesis of 7-Hydroxymurrayazolinine, Murrayamine D, and Mahanine via m-Nitro Group Activated Pyran Annulation.
The facile total synthesis of the natural product (±)-mahanine was obtained in eight steps with an overall 52% yield from readily accessible known nitrophenol derivative 6. After a one-step, acid-catalyzed annulation, two additional natural products were formed including 7-hydroxymurrayazolinine, representing its first reported total synthesis. In the whole process, the introduction of the m-nitro group significantly enhanced the key pyran annulation reaction through inductive effects.
Center for Drug Discovery, Georgetown University Medical Center, Research Building, EP07, 3970 Reservoir Road, NW, Washington, D.C. 20057, United States.
Shujie
S
Hou
Center for Drug Discovery, Georgetown University Medical Center, Research Building, EP07, 3970 Reservoir Road, NW, Washington, D.C. 20057, United States.
Yong
Y
Liu
Center for Drug Discovery, Georgetown University Medical Center, Research Building, EP07, 3970 Reservoir Road, NW, Washington, D.C. 20057, United States.
Yali
Y
Kong
Center for Drug Discovery, Georgetown University Medical Center, Research Building, EP07, 3970 Reservoir Road, NW, Washington, D.C. 20057, United States.
Milton L
ML
Brown
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
C568219:7-hydroxymurrayazolinine; D000470:Alkaloids; D001688:Biological Products; D002227:Carbazoles; D006576:Heterocyclic Compounds, 4 or More Rings; D009574:Nitro Compounds; D011714:Pyrans; C465290:mahanine; C000601876:murrayamine D