Exploring chemical diversity of epoxyquinoid natural products: synthesis and biological activity of (-)-jesterone and related molecules.
Enantioselective syntheses of the potent antifungal agent (-)-jesterone, its hydroxy epimer, and a dimeric quinone epoxide derivative are reported. The synthesis involves diastereoselective epoxidation of a chiral quinone monoketal derivative and regio- and stereoselective reduction of a quinone epoxide intermediate.
Hu
Y
Y
Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA.
Li
C
C
Kulkarni
B A
BA
Strobel
G
G
Lobkovsky
E
E
Torczynski
R M
RM
Porco
J A
JA
D000475:Alkenes / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008958:Models, Molecular; D013237:Stereoisomerism
D000475:Alkenes; D000935:Antifungal Agents; D004852:Epoxy Compounds; D007202:Indicators and Reagents; C431025:jesterone