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

Chi Yun Liu, Venkatachalam Angamuthu, Wei Chen Chen, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

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.

Original languageEnglish
Pages (from-to)2246-2250
Number of pages5
JournalOrganic Letters
Volume22
Issue number6
DOIs
StatePublished - 20 Mar 2020

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