title: Crotylation versus propargylation: two routes for the synthesis of the C13-C18 fragment of the antibiotic branimycin.
abstract: The C13-C18 fragment 3 of the novel antibiotic branimycin was prepared along two highly stereocontrolled routes. The first one uses a standard Roush crotylation protocol, whereas the second one proceeds via an allenyl silane propargylation with unexpected stereochemical consequences, which are discussed in detail.
authors.affiliation: Institut für Organische Chemie, Universität Wien, Währingerstrasse 38, 1090 Vienna, Austria.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Felzmann
authors.forename: Daniele
authors.initials: D
authors.lastname: Castagnolo
authors.forename: Daniela
authors.initials: D
authors.lastname: Rosenbeiger
authors.forename: Johann
authors.initials: J
authors.lastname: Mulzer
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000480:Alkynes; D000900:Anti-Bacterial Agents; D018942:Macrolides; D012821:Silanes; C516575:branimycin; C507609:crotylsilane