Three-component one-pot total syntheses of glyantrypine, fumiquinazoline F, and fiscalin B promoted by microwave irradiation.
A microwave-promoted three-component one-pot reaction has been developed to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to several families of alkaloids with significant biological activities. By adapting this synthetic strategy through the use of selected Boc-amino acids and amino acid esters, we have accomplished highly efficient and concise total syntheses of glyantrypine (2), fumiquinazoline F (3), and fiscalin B (5), achieving overall yields of 55, 39, and 20%, respectively.
Liu
Ji-Feng
JF
ArQule, Inc., Division of Chemical Technologies, 19 Presidential Way, Woburn, Massachusetts 01801, USA. jliu@arqule.com
Ye
Ping
P
Zhang
Bailin
B
Bi
Grace
G
Sargent
Katie
K
Yu
Libing
L
Yohannes
Daniel
D
Baldino
Carmen M
CM
D000470:Alkaloids / Q000737:chemistry; D001685:Biological Factors / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D013058:Mass Spectrometry; D008872:Microwaves; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000470:Alkaloids; D001685:Biological Factors; D007211:Indoles; D011799:Quinazolines; C081408:fiscalin B; C504706:fumiquinazoline F; C075514:glyantrypine; D014364:Tryptophan