P-heterocyclic building blocks: application to the stereoselective synthesis of P-sugars.
A strategy relying on the utilization of stereoselective additions to allyldiphenylphosphonate esters and subsequent ring-closing metathesis (RCM) to access P-chiral P-heterocyclic building blocks for the synthesis of phosphono sugars is described. These building blocks possess several attractive components, including the following: (i) P(2) and C(6) stereogenic centers for directing stereoselective transformations; (ii) an activated C(3) methylene group that promotes base-mediated olefin transposition to generate vinyl phosphonates available for further stereoselective reactions; and (iii) a P(2)-stereogenic center containing an exchangeable phosphonate ester armed to attenuate the "stereochemical environment" at phosphorus. Taken collectively, these attributes contribute to a concise method for the stereoselective synthesis of an array of P-sugars.
Stoianova
Diana S
DS
Department of Chemistry, 1251 Wescoe Hall Drive, Malott Hall, University of Kansas, Lawrence, KS 66045-7582, USA.
Whitehead
Alan
A
Hanson
Paul R
PR
D002241:Carbohydrates / Q000138:chemical synthesis*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D008956:Models, Chemical; D063065:Organophosphonates / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*; D013237:Stereoisomerism
D002241:Carbohydrates; D006571:Heterocyclic Compounds; D063065:Organophosphonates; D010758:Phosphorus