Synthesis of (+/-)-epoxysorbicillinol using a novel cyclohexa-2,5-dienone with synthetic applications to other sorbicillin derivatives.
A novel route to epoxysorbicillinol as well as dimers of sorbicillin is reported. The synthesis is-in principle-amenable to enantioselectivity. The key step is an oxidative dearomatization to produce a stable and highly malleable p-quinol intermediate, which undergoes a highly diastereoselective epoxidation.
Pettus
L H
LH
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106, USA. pettus@chem.ucsb.edu
Van De Water
R W
RW
Pettus
T R
TR
D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D019281:Dimerization; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D003512:Cyclohexanones; D004852:Epoxy Compounds; D007202:Indicators and Reagents; C426423:epoxysorbicillinol