Stereoselective ketal-tethered intramolecular diels-alder cycloadditions. An approach to the 2-oxadecalin spiroketal core of antifungal agent fusidilactone C.
[reaction: see text] An approach toward the 2-oxadecalin spiroketal core of fusidilactone C via a rare ketal-tethered intramolecular Diels-Alder cycloaddition is described here. This intramolecular Diels-Alder cycloaddition is highly endo-selective and overall depended upon the nature of solvents and Lewis acids. We also observed some remarkable rate acceleration in MeOH.
Wang
Jiashi
J
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Hsung
Richard P
RP
Ghosh
Sunil K
SK
D000935:Antifungal Agents / Q000138:chemical synthesis*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009281:Naphthalenes / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000935:Antifungal Agents; D007783:Lactones; D009281:Naphthalenes; D013141:Spiro Compounds; C498382:fusidilactone A; C498381:fusidilactone C; C449320:oxadecalin