title: PhI(OAc)2-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: synthesis of norharmane, harmane, eudistomin U and eudistomin I.
abstract: Iodobenzene diacetate was employed as a mild and efficient reagent for one-pot oxidative decarboxylation of tetrahydro-β-carboline acids and dehydrogenation of tetrahydro-β-carbolines to access the corresponding aromatic β-carbolines. To the best of our knowledge this is the first synthesis of β-carbolines via a one-pot oxidative decarboxylation at ambient temperature. The utility of this protocol has been demonstrated in the synthesis of β-carboline alkaloids norharmane (2o), harmane (2p), eudistomin U (9) and eudistomin I (12).
authors.affiliation: Medicinal Chemistry & Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. ahmedkamal@iict.res.in.
authors.forename: Ahmed
authors.initials: A
authors.lastname: Kamal
authors.forename: Yellaiah
authors.initials: Y
authors.lastname: Tangella
authors.forename: Kesari Lakshmi
authors.initials: KL
authors.lastname: Manasa
authors.forename: Manda
authors.initials: M
authors.lastname: Sathish
authors.forename: Vunnam
authors.initials: V
authors.lastname: Srinivasulu
authors.forename: Jadala
authors.initials: J
authors.lastname: Chetna
authors.forename: Abdullah
authors.initials: A
authors.lastname: Alarifi
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry*; D003653:Decarboxylation; D006247:Harmine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000085:Acetates; D002243:Carbolines; D007462:Iodobenzenes; C088110:eudistomin U; C008857:phenyliodosodiacetate; D006247:Harmine; C009804:tryptoline; C005010:harman; C056222:eudistomin I; C010262:norharman