ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
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
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.
Chemical Papers 71 (4) 709–719 (2017)
Thursday, February 27, 2020