Synthesis of azacridone A.
[reaction: see text] The first total synthesis of the only known naturally occurring azaacridone alkaloid (1) has been achieved in 10 steps from phloroglucinol. A variety of ortholithiation reactions are described, and a method for overcoming the originally unfavorable regiochemistry of one of them is provided.
Scopton
Alex
A
E. F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Kelly
T Ross
TR
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D011799:Quinazolines; C508467:azacridone A