Synthesis of 8-desbromohinckdentine A1.
Hinckdentine A is an alkaloid isolated from the bryozoan Hincksinoflustra denticulate. This natural product contains a novel and unique 11b,12,13,14,15,16-hexahydroazepino[4',5':2,3]indolo[1,2-c]quinazoline ring system that has not previously been synthesized. We have synthesized 8-desbromohinckdentine A from a 2-aryl indole by first preparing the quaternary center of the natural product and then building the seven-membered lactam and dihydropyrimidine rings onto this intermediate to form the framework of hinckdentine A.
Liu
Yahua
Y
Medicinal Chemistry Research, Pharmacia Corporation, Kalamazoo, Michigan 49001, USA.
McWhorter
William W
WW
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D002013:Bryozoa / Q000737:chemistry; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis*
C473967:8-desbromohinckdentine A; D000470:Alkaloids; D007211:Indoles; D011799:Quinazolines