title: Synthesis of the tricyclic core of manzamine A.
abstract: An efficient synthetic approach to the core structure of the manzamine alkaloids is reported, particularly in relation to incorporating a one-carbon unit in ring B from which the aldehyde in ircinal A or the beta-carboline unit in manzamine A could potentially be generated. The key steps involve a Johnson-Claisen rearrangement, enolate alkylation, dithiane alkylation and a stereoselective intramolecular dipolar cycloaddition of an azomethine ylide, which provided the desired tricyclic ABC core structure.
authors: Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK. i.coldham@sheffield.ac.uk.
authors: Ravindra B
authors: RB
authors: Pathak
authors: Benjamin C
authors: BC
authors: Dobson
authors: Nandita
authors: N
authors: Ghosh
authors: Khalid A
authors: KA
authors: Ageel
authors: Madeha R
authors: MR
authors: Alshawish
authors: Rungroj
authors: R
authors: Saruengkhanphasit
authors: Iain
authors: I
authors: Coldham
mesh_terms: D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D002227:Carbazoles; C078290:manzamine A