Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 15, Pages 5880-5889Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0505122
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Funding
- NIGMS NIH HHS [R01 GM 58103] Funding Source: Medline
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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.
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