Expanding the scope of Mn(OAc)3-mediated cyclizations: synthesis of the tetracyclic core of tronocarpine.
Pyrroles, indoles, and surprisingly, indolines, when equipped with a pendant malonyl group on the nitrogen atom, were effective substrates in a Mn(III)-mediated oxidative cyclization reaction, yielding the 1,2-annulated products in good to excellent yields. When indole acetonitrile was used as a substrate this method provided a rapid synthesis of a tetracyclic tronocarpine subunit.
Magolan
Jakob
J
Department of Chemistry, University of Western Ontario, London, Ontario, Canada N6A 5B7.
Kerr
Michael A
MA
D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D017895:Manganese Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction
D001381:Azepines; D026121:Indole Alkaloids; D017895:Manganese Compounds; C520942:tronocarpine