title: Gold-catalyzed one-step construction of 2,3-dihydro-1H-Pyrrolizines with an electron-withdrawing group in the 5-position: a formal synthesis of 7-methoxymitosene.
abstract: What a ring formation! Bicyclic dihydropyrrolizines with an electron-withdrawing group (EWG) at the 5-position are formed in one step from linear azidoenynes under gold catalysis. This novel route involves the use of azide as a nitrene precursor, electronically-controlled regioselectivity, and the generation of destabilized 1-azapentadienium ions and their pericyclic reactions. This method was used for a formal synthesis of 7-methoxymitosene.
authors: Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA.
authors: Ze-Yi
authors: ZY
authors: Yan
authors: Yuanjing
authors: Y
authors: Xiao
authors: Liming
authors: L
authors: Zhang
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D006046:Gold / Q000737:chemistry*; D008937:Mitomycins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D008937:Mitomycins; D011758:Pyrroles; D006046:Gold