Microwave-Assisted Concise Total Syntheses of Quinazolinobenzodiazepine Alkaloids
The Journal of Organic Chemistry2005Vol. 70(25), pp. 10488–10493
Citations Over TimeTop 13% of 2005 papers
Jifeng Liu, Mira Kaselj, Yuko Isome, Jennifer Chapnick, Bailin Zhang, Grace Bi, Daniel Yohannes, Libing Yu, Carmen M. Baldino
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.
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