title: Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids.
abstract: [reactions: see text] One-pot total syntheses of the quinazolinobenzodiazepine alkaloids sclerotigenin (1), (+/-)-circumdatin F (2), and (+/-)-asperlicin C (3) via novel microwave-assisted domino reactions were achieved in 55%, 32%, and 20% yields, respectively, from commercially available starting materials. A two-step total synthesis of (+/-)-benzomalvin A (4) was accomplished with an overall yield of 16%. Additionally, analogues of circumdatin E were synthesized via the three-component one-pot sequential reactions promoted by microwave irradiation. Finally, a two-step formal total synthesis of (+/-)-asperlicin E (5) was also realized by using this microwave-assisted protocol.
authors.affiliation: ArQule, Inc., Division of Chemical Technologies, 19 Presidential Way, Woburn, Massachusetts 01801, USA. jliu@arqule.com
authors.forename: Ji-Feng
authors.initials: JF
authors.lastname: Liu
authors.forename: Mira
authors.initials: M
authors.lastname: Kaselj
authors.forename: Yuko
authors.initials: Y
authors.lastname: Isome
authors.forename: Jennifer
authors.initials: J
authors.lastname: Chapnick
authors.forename: Bailin
authors.initials: B
authors.lastname: Zhang
authors.forename: Grace
authors.initials: G
authors.lastname: Bi
authors.forename: Daniel
authors.initials: D
authors.lastname: Yohannes
authors.forename: Libing
authors.initials: L
authors.lastname: Yu
authors.forename: Carmen M
authors.initials: CM
authors.lastname: Baldino
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D001569:Benzodiazepines / Q000138:chemical synthesis*; D001570:Benzodiazepinones / Q000138:chemical synthesis; D008722:Methods; D008872:Microwaves; D011744:Pyrimidinones / Q000138:chemical synthesis; D011799:Quinazolines / Q000138:chemical synthesis*
chemical_list: D000470:Alkaloids; D001570:Benzodiazepinones; D011744:Pyrimidinones; D011799:Quinazolines; C428194:circumdatin F; D001569:Benzodiazepines; C088520:benzomalvin A; C057103:asperlicin E; C057101:asperlicin C