ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A Lemieux–Johnson oxidation of shikimic acid derivatives: facile entry to small library of protected (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals

Miroslav Psotka, Miroslava Martinková, and Jozef Gonda

Department of Organic Chemistry, Institute of Chemical Sciences, P. J. Šafárik University, Košice, Slovak Republic

E-mail: jozef.gonda@upjs.sk

Abstract: The Lemieux–Johnson oxidation was employed for the cleavage of the carbon–carbon double bond of shikimic acid derivatives. Through this procedure, a series of the sixteen novel (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals bearing three contiguous stereocentres have been synthesized in excellent yields.

Keywords: Shikimic acid; Lemieux-Jonson oxidation; 6-oxoheptanals

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-016-0004-8

Chemical Papers 71 (4) 709–719 (2017)