Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids.
[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.
Liu
Ji-Feng
JF
ArQule, Inc., Division of Chemical Technologies, 19 Presidential Way, Woburn, Massachusetts 01801, USA. jliu@arqule.com
Kaselj
Mira
M
Isome
Yuko
Y
Chapnick
Jennifer
J
Zhang
Bailin
B
Bi
Grace
G
Yohannes
Daniel
D
Yu
Libing
L
Baldino
Carmen M
CM
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*
D000470:Alkaloids; D001570:Benzodiazepinones; D011744:Pyrimidinones; D011799:Quinazolines; C428194:circumdatin F; D001569:Benzodiazepines; C088520:benzomalvin A; C057103:asperlicin E; C057101:asperlicin C