title: Synthesis of a leucomitosane via a diastereoselective radical cascade.
abstract: The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones with excellent diastereomeric ratios. The radical cascade/lactamization sequence was efficiently applied to the synthesis of a 3-oxo-leucomitosane related to the mitomycin family of alkaloids.
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
authors.forename: François
authors.initials: F
authors.lastname: Brucelle
authors.forename: Philippe
authors.initials: P
authors.lastname: Renaud
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D007461:Iodoacetates / Q000737:chemistry; D008937:Mitomycins / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D000081248:Allylbenzene Derivatives
chemical_list: D000498:Allyl Compounds; D001555:Benzene Derivatives; D001880:Boranes; D007211:Indoles; D007461:Iodoacetates; D008937:Mitomycins; C102347:allylbenzene; D000081248:Allylbenzene Derivatives; C079756:triethylborane