American Chemical Society
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Microwave-Assisted Concise Total Syntheses of Quinazolinobenzodiazepine Alkaloids

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journal contribution
posted on 2005-12-09, 00:00 authored by Ji-Feng Liu, Mira Kaselj, Yuko Isome, Jennifer Chapnick, Bailin Zhang, Grace Bi, Daniel Yohannes, Libing Yu, Carmen M. Baldino
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.