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

(2S,3R)-3-하이드록시호모세린락톤의 입체선택적 합성 : 바이닐글라이신 OBO Ester 유도체의 입체선택적인 이중알콜화 반응

  • 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)
  • 고무현 (서울대학교 공과대학 화학생물공학부) ;
  • 전종호 (경북대학교 공과대학 응용화학공학부 응용화학전공) ;
  • 김영규 (서울대학교 공과대학 화학생물공학부)
  • Received : 2020.03.04
  • Accepted : 2020.03.11
  • Published : 2020.04.10

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.

Acknowledgement

Supported by : Kyungpook National University

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