title: Regiodivergent and short total synthesis of calothrixins.
abstract: The anionic annulation of MOM-protected furoindolone with 4-bromoquinoline followed by deprotection of the N-MOM group provides calothrixin B, whereas that with 3-bromoquinoline yields isocalothrixin B. The outcomes are explained by the divergence of the reaction mechanism from commonly perceived quinolyne intermediate. A sequence of addition-cyclization-elimination is proposed to account for the formation of calothrixin from 4-bromoquinoline.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur-721302, India. dmal@chem.iitkgp.ernet.in.
authors.forename: Dipakranjan
authors.initials: D
authors.lastname: Mal
authors.forename: Joyeeta
authors.initials: J
authors.lastname: Roy
authors.forename: Kumar
authors.initials: K
authors.lastname: Biradha
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C418327:calothrixin B