Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids

被引：73

作者：

Liu, JF ^{[1
]}

Kaselj, M ^{[1
]}

Isome, Y ^{[1
]}

Chapnick, J ^{[1
]}

Zhang, BL ^{[1
]}

Bi, G ^{[1
]}

Yohannes, D ^{[1
]}

Yu, LB ^{[1
]}

Baldino, CM ^{[1
]}

机构：

[1] ArQule Inc, Div Chem Technol, Woburn, MA 01801 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 25期

关键词：

D O I：

10.1021/jo051876x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

;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.

引用

页码：10488 / 10493

页数：6

共 33 条

[1] Sceptrin as a potential biosynthetic precursor to complex pyrrole - Pyrrole-imidazole alkaloids: The total synthesis of ageliferin [J].