We have accomplished the first total synthesis of (+/-)-hinckdentine A (1). The key steps are m-CPBA oxidation of 2-arylindole followed by acid-mediated Mannich-type C-C bond formation of 2-hydroxyindolin-3-one, seven-membered ring closure, and regioselective tribromination.
Alkaloids U 0600First Total Synthesis of Hinckdentine A (VI). -Key step is the construction of a quaternary carbon center by acid-mediated Mannich-type reaction of 2-hydroxyindolin-3-one (I) -(HIGUCHI, K.; SATO, Y.; TSUCHIMOCHI, M.; SUGIURA, K.; HATORI, M.; KAWASAKI*, T.; Org. Lett. 11 (2009) 1, 197-199; Meiji Pharm. Univ.,
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.