A desymmetrization approach toward highly oxygenated cis-decalins.
The cis-decalin core 2 of the antibiotic branimycin has been prepared by desymmetrization of diepoxynaphthalene 4. The key steps involve two successive S(N)' opening of the oxa-bridges. An improved procedure for the synthesis of 4 is also described.
Gromov
Alexey
A
University of Vienna, Institute of Organic Chemistry, Wahringerstrasse 38, A-1090 Vienna, Austria. alexey.gromov@univie.ac.at
Enev
Valentin
V
Mulzer
Johann
J
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D018942:Macrolides; D009281:Naphthalenes; C516575:branimycin; C007229:decalin