Concise Total Syntheses of Pyr­ido[4, 3‐b]carbazole Alkaloids Using Copper‐Mediated 6π‐Electrocyclization. Issue 13 (13th April 2016)

• Record Type: Journal Article
• Authors: Itoh, Tomoki; Abe, Takumi; Choshi, Tominari; Nishiyama, Takashi; Yanada, Reiko; Ishikura, Minoru
• Is Part Of: European journal of organic chemistry. Issue 13(2016)
• Page Start: 2290
• Page End: 2299
• Publication Date: 2016-04-13
• Subjects: Total synthesis -- Natural products -- Alkaloids -- Nitrogen heterocycles -- Electrocyclization -- Copper; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600246
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Concise syntheses of 9‐methoxyellipticine, 3, 4‐dihydroellipticine (µ‐alkaloid D), 1, 2, 3, 4‐tetrahydroellipticine, 2‐methyl‐1, 2, 3, 4‐tetrahydroellipticine, olivacine, 3, 4‐dihydroolivacine, (±)‐guatambuine, and (±)‐janetine were developed starting from hexatriene intermediates readily obtained by Pd‐catalyzed tandem cyclization/cross‐coupling reaction of indolylborates. The route enables the facile construction of pyrido[4, 3‐ b ]carbazoles by Cu‐catalyzed 6π‐electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4, 3‐ b ]carbazole alkaloids. Abstract : Concise total syntheses of pyrido[4, 3‐ b ]carbazole alkaloids were accomplished using Cu‐catalyzed 6π‐electrocyclization of hexatriene as a key step.