Crotylation versus propargylation: two routes for the synthesis of the C13-C18 fragment of the antibiotic branimycin.
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.
Felzmann
Wolfgang
W
Institut für Organische Chemie, Universität Wien, Währingerstrasse 38, 1090 Vienna, Austria.
Castagnolo
Daniele
D
Rosenbeiger
Daniela
D
Mulzer
Johann
J
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
D000475:Alkenes; D000480:Alkynes; D000900:Anti-Bacterial Agents; D018942:Macrolides; D012821:Silanes; C516575:branimycin; C507609:crotylsilane