title: Studies towards the total synthesis of batzelladine A.
abstract: Application of a diastereoselective three-component coupling to the bicyclic core of the batzelladine alkaloids is described. The synthesis features the elaboration of glutamic acid by use of Eschenmoser sulfide contraction. An earlier approach is also included, which shows some limitations of dithiane chemistry when applied to the particular compounds required for this target.
authors.affiliation: School of Chemistry, Cardiff University, PO Box 912, Cardiff, UKCF10 3TB. elliottmc@cardiff.ac.uk
authors.forename: Mark C
authors.initials: MC
authors.lastname: Elliott
authors.forename: Matthew S
authors.initials: MS
authors.lastname: Long
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D019791:Guanidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006146:Guanidines / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006146:Guanidines; D011743:Pyrimidines; C438977:batzelladine A; C492936:batzelladine B; C410707:batzelladine D; C444860:batzelladine F; C492937:crambescin A; C103200:ptilomycalin A; D019791:Guanidine