Synthesis of (-)-chaetominine.
The tricyclic hydroxy imidazolidinone was converted to chaetominine in seven steps in 22% overall yield. The key step was the construction of the delta-lactam by heating an amino ester with a catalytic amount of DMAP in toluene at reflux.
Snider
Barry B
BB
Department of Chemistry MS 015, Brandeis University, Waltham, MA 02454-9110, USA. snider@brandeis.edu
Wu
Xiaoxing
X
D000586:Amination; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D048289:Imidazolidines / Q000138:chemical synthesis / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D011799:Quinazolines / Q000737:chemistry
D001688:Biological Products; D048289:Imidazolidines; D026121:Indole Alkaloids; D007769:Lactams; D007783:Lactones; D011799:Quinazolines; C522312:chaetominine; C419468:fumiquinazoline A