First total synthesis of xestobergsterol A and active structural analogues of the xestobergsterols.
[formula: see text] A novel pentacyclic polyhydroxylated sterol, xestobergsterol A (1a), has been synthesized in 24 steps and in good overall yield from stigmasterol 17. The key steps of the synthesis are the Breslow remote functionalization of the polyoxygenated steroid derived from 25 and the base-catalyzed epimerization-aldol condensation of the dione derived from 27.
Jung
M E
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles 90095-1569, USA. jung@chem.ucla.edu
Johnson
T W
TW
D002240:Carbohydrate Sequence; D002778:Cholestanones / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D013261:Sterols / Q000737:chemistry; D013265:Stigmasterol / Q000737:chemistry*
D002778:Cholestanones; D013261:Sterols; C079916:xestobergsterol A; D013265:Stigmasterol