Toward the synthesis of the antibiotic branimycin: novel approaches to highly substituted cis-decalin systems.
A variety of highly functionalized cis-decalin systems have been prepared by means of the stereoselective transannular Diels-Alder (TADA) reaction of a (Z,E,Z,Z)-tetraene macrolide, and by means of intramolecular nitrile oxide olefin (INOC) or ring-closing metathesis (RCM) annulations to quinic acid derivatives.
Mulzer
Johann
J
Institut für Organische Chemie, Universität Wien, Währinger Strasse 38, 1090 Wien, Austria. johann.mulzer@univie.ac.at
Castagnolo
Daniele
D
Felzmann
Wolfgang
W
Marchart
Stefan
S
Pilger
Christian
C
Enev
Valentin S
VS
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D018942:Macrolides; D009281:Naphthalenes; C516575:branimycin; C007229:decalin