A non-Diels-Alder approach to the cis-decalin core of branimycin.
The synthesis of the highly substituted cis-decalin core of branimycin has been accomplished. A catalytic copper mediated SN2' opening of oxabicycle 7 with Grignard reagent and ring-closing metathesis served as key transformations.
Enev
Valentin S
VS
Institut für Organische Chemie, Währingerstrasse 38, A-1090 Wien, Austria. valentin.enev@univie.ac.at
Drescher
Martina
M
Mulzer
Johann
J
D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D003516:Cycloparaffins / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D003516:Cycloparaffins; D018942:Macrolides; D009281:Naphthalenes; C516575:branimycin; D003300:Copper; C007229:decalin