title: Selective formation of a Z-trisubstituted double bond using a 1-(tert-butyl)tetrazolyl sulfone.
abstract: In our effort to gain further insight into the enantioselective synthesis of the structural core of phormidolides B and C, we have discovered the formation of a Z-trisubstituted double bond. Here, we describe a highly selective process that can be applied to our target following a strategy that is based on Julia-Kocienski olefination. The use of 1-(tert-butyl)tetrazolyl sulfone affords the construction of the Z-trisubstituted alkene with high efficiency and stereoselectivity.
authors.affiliation: Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona , Baldiri Reixac 10, 08028 Barcelona, Spain.
authors.forename: Adriana
authors.initials: A
authors.lastname: Lorente
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.forename: Mercedes
authors.initials: M
authors.lastname: Álvarez
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013450:Sulfones / Q000737:chemistry*; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: C000596131:1-(tert-butyl)tetrazolyl sulfone; D000475:Alkenes; D018942:Macrolides; D013450:Sulfones; D013777:Tetrazoles; C000596130:phormidolide B; C000596129:phormidolide C