Progress toward the synthesis of hinckdentine A.
Hinckdentine A is a structurally unique marine alkaloid containing an 11b,12,13,14,15,16-hexahydroazepino[4',5':2,3] indolo[1,2-c]quinazoline ring system. This review covers the literature on hinckdentine A. The indolo[1,2-c]quinazoline ring system is the foundation of the hinckdentine A structure. The literature on the chemistry of indoloquinazolines until the end of 1994 has been reviewed by Billimoria and Cava. Therefore, we review the research carried out on the synthesis of indolo[1,2-c]quinazolines and related ring systems in which hinckdentine A is described from 1995 to present. The construction of the quaternary center is the primary synthetic challenge posed by the hinckdentine A structure. We will present a selection of methods applicable to the synthesis of 2,2-disubstituted indolines. Finally, we present the three most significant attempts to synthesize hinckdentine A.
McWhorter
William W
WW
Genomics Institute of the Novartis Research Foundation, Medicinal Chemistry, San Diego, CA 92121-1127, USA. will.mcwhorter@worldnet.att.net
Liu
Yahua
Y
D000818:Animals; D002013:Bryozoa; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D011799:Quinazolines / Q000138:chemical synthesis*; D013678:Technology, Pharmaceutical / Q000379:methods / Q000639:trends*
D026121:Indole Alkaloids; D011799:Quinazolines; C485801:hinckdentine A