Synthesis of Methyl l-Kijanosides by Regio- and Stereoselective Ring Opening of 2-Oxazolidinone - Fused Aziridines

Org Lett. 2020 Mar 20;22(6):2246-2250. doi: 10.1021/acs.orglett.0c00443. Epub 2020 Mar 2.

Abstract

Kijanose is one of the most highly functionalized deoxysugars found in nature and a challenging synthetic target. We found that the ring opening of trisubstituted, 2-oxazolidinone-fused aziridines is regio- and stereoselective, and the azide adduct has the same stereochemistry as that of kijanose after converting the azido to a nitro group. Therefore, both α- and β-methyl l-kijanosides were prepared from ethyl l-lactate in 14% total yield.

Publication types

  • Research Support, Non-U.S. Gov't