Novel one-pot total syntheses of deoxyvasicinone, mackinazolinone, isaindigotone, and their derivatives promoted by microwave irradiation.
[reaction: see text]. Total syntheses of deoxyvasicinone (1), mackinazolinone (2), and 8-hydroxydeoxyvasicinone (3) via novel microwave-assisted domino reactions, as well as a novel three-component one-pot total synthesis of isaindigotone (5) promoted by microwave irradiation, are reported. The efficient reaction process enabled us to rapidly access related natural product derivatives and to identify a new class of cytotoxic agents.
Liu
Ji-Feng
JF
ArQule, Inc., Woburn, Massachusetts 10801, USA.
Ye
Ping
P
Sprague
Kevin
K
Sargent
Katie
K
Yohannes
Daniel
D
Baldino
Carmen M
CM
Wilson
Christopher J
CJ
Ng
Shi-Chung
SC
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D052999:Quinazolinones; D011827:Radiation
D000470:Alkaloids; D011799:Quinazolines; D052999:Quinazolinones; C440668:isaindigotone; C510340:mackinazolinone; C025696:2,3-trimethylene-4-quinazolone