Access to electron-rich arene-fused hexahydroquinolizinones through a gold-catalysis-initiated cascade process.
Golden Cascade: With a tethered, electron-rich arene as the internal nucleophile, a gold-catalyzed amide cyclization to an alkyne initiates a cascade process that ends with a Ferrier rearrangement. Electron-rich arene-bearing hexahydroquinolizin-2-ones are formed in good yields and can be converted into indole alkaloids in only a few steps.
Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA.
Lianzhu
L
Liu
Liming
L
Zhang
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004583:Electrons; D006046:Gold / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry*
D000577:Amides; D006841:Hydrocarbons, Aromatic; D026121:Indole Alkaloids; D011807:Quinolizines; D006046:Gold