title: Enantioselective organocatalytic construction of hexahydropyrroloindole by means of α-alkylation of aldehydes leading to the total synthesis of (+)-gliocladin C.
abstract: 12-step program: The combined use of cinchona alkaloid based amine and chiral phosphoric acid enabled the asymmetric alkylation reaction of 3-hydroxyoxindoles with aldehydes to give 3,3'-disubstituted oxindoles in excellent enantioselectivities, which allows for the enantioselective total synthesis of (+)-gliocladin C in 12 steps from 3-hydroxyoxindole with 19 % overall yield (see scheme; PMB = para-methoxybenzyl).
authors: Microscale Joint Laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, PR China.
authors: Jin
authors: J
authors: Song
authors: Chang
authors: C
authors: Guo
authors: Arafate
authors: A
authors: Adele
authors: Hao
authors: H
authors: Yin
authors: Liu-Zhu
authors: LZ
authors: Gong
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000478:Alkylation; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003500:Cyclization; D007941:Leukemia P388; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000470:Alkaloids; D000970:Antineoplastic Agents; D010879:Piperazines; D011760:Pyrrolidinones; C518056:gliocladin C