Synthesis of 6-Hydroxyalkylidenepenicillanates

6-히드록시알킬리덴페니실란산 염의 합성

  • Lee, Jung Hwan (Department of Chemistry, Seoul National University) ;
  • Ko, Jae Young (Department of Chemistry, Seoul National University) ;
  • Seo, Kyung Jae (Department of Chemistry, Seoul National University) ;
  • Goo, Yang Mo (Department of Pharmacy, Seoul National University) ;
  • Lee, Youn Young (Department of Chemistry, Seoul National University)
  • 이중환 (서울대학교 자연과학대학 화학과) ;
  • 고재영 (서울대학교 자연과학대학 화학과) ;
  • 서경재 (서울대학교 자연과학대학 화학과) ;
  • 구양모 (서울대학교 약학대학 약학과) ;
  • 이윤영 (서울대학교 자연과학대학 화학과)
  • Published : 19990800

Abstract

Allyl (5R)-(Z)- and (5R)-(E)-6-[(2S)-2,3-isopropylidenedioxypropylidene]Penicillanate(10a and 10b) were prepared from allyl (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with 2,3-O-isopropylidene-D-glyceraldehyde, reduction with $Zn-NH_4OAc$, and Mitsunobu elimination. Deprotection of isopropylidene and allyl groups of 10a gave potassium (5R)-(Z)-6-[(2S)-2,3-dihydroxypropylidene]penicillanate(4). However, deprotection of isopropylidene group of 10b afforded ${\alpha},\;{\beta}$-unsaturated-lactone(12). Allyl (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-(t-butyldimethlsilyloxy)propylidene]penicillanate(18a and 18b) were prepared from ally (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with (2S)-2-(t-butyldimethylsilyloxy)propanal(15), reduction with $Zn-NH_4OAc$ and Mitsunobu elimination or mesylation-elimination. Deprotection of t-butyldimethylsilyl and allyl groups of 18a and 18b gave potassium (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-hydroxypropylidene]penicillanate(5a and 5b), respectively.

Keywords

References

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