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http://dx.doi.org/10.14478/ace.2020.1019

Stereoselective Synthesis of (2S,3R)-3-Hydroxyhomoserine Lactone via anti Selective Dihydroxylation of an OBO Group-Protected Vinyl Glycine Analog  

Koh, Moo-hyun (School of Chemical and Biological Engineering, Seoul National University)
Jeon, Jongho (Department of Applied Chemistry, School of Applied Chemical Engineering, Kyungpook National University)
Kim, Young Gyu (School of Chemical and Biological Engineering, Seoul National University)
Publication Information
Applied Chemistry for Engineering / v.31, no.2, 2020 , pp. 187-192 More about this Journal
Abstract
(2S,3R)-3-hydroxyhomoserine lactone (HSL) has been used as a key intermediate for the synthesis of various biologically active compounds. In this study, we demonstrated an efficient synthesis of HSL via anti selective dihydroxylation of a protected vinyl glycine analog with an oxabicyclo[2.2.2]octyl orthoester (OBO) ester group. Because the acyclic conformation of the substrate was efficiently controlled by the bulky OBO ester group, a diastereoselectivity of > 10 : 1 was obtained in the dihydroxylation reaction without the use of a chiral reagent. By using this result, the target compound 1 can be obtained from commercially available N-Cbz-L-serine 2 in seven steps with an overall yeid of 34%. This result could be applied to the stereoselective synthesis of biologically active molecules containing a vicinal amino diol moiety.
Keywords
(2S,3R)-3-Hydroxyhomoserine lactone; Dihydroxylation; Vinyl glycine analog; Stereoselective synthesis; OBO ester;
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