YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Synthesis of 6-Exomethylene Penams with Benzothiazole Ring

Benzothiazole고리가 있는 6-엑소메칠렌 펜남 유도체의 합성

  • 임채욱 (중앙대학교 약학대학 의약화학 교실) ;
  • 박희석 (중앙대학교 약학대학 의약화학 교실) ;
  • 김승재 (중앙대학교 약학대학 의약화학 교실) ;
  • 임철부 (중앙대학교 약학대학 의약화학 교실)
  • Published : 2002.10.01
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Abstract

The synthesis of new 6-exomethylene penams with benzothiazole ring was described. The 6,6-dibromopenam 5 was treated with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was reacted with acetic anhydride to give acetoxy compound 7. The deacetobromination of acetoxy compound 7 with zinc and acetic acid gave 6-exomethylene penams, Z-isomer 8 and E-isomer 9, which was oxidized to sulfones 10 by m-CPBA. The p-methoxybenzyl compounds 6~10 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 11~15.

Keywords

References

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