Rapid stereocontrolled assembly of the fully substituted C-aryl glycoside of kendomycin with a Prins cyclization: a formal synthesis.
Prins cyclization using an electron-rich benzaldehyde and a homoallylic alcohol efficiently delivered the fully substituted C-aryl tetrahydropyranoside of kendomycin.
Bahnck
Kevin B
KB
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, Irvine, CA 92697, USA.
Rychnovsky
Scott D
SD
D001547:Benzaldehydes / Q000737:chemistry; D003500:Cyclization; D004583:Electrons; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D020005:Propanols / Q000737:chemistry; D017828:Rifabutin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D001547:Benzaldehydes; D006027:Glycosides; D020005:Propanols; C485395:kendomycin; D017828:Rifabutin; C006463:allyl alcohol; C032175:benzaldehyde