Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis of a Precursor of Bulgecinine, (4S,5R)-1-Acetyl-2-formyl-5-benzyloxymethyl-4-pyrrolidinol

Bulgecinine 선구물질인 (4S,5R)-1-Acetyl-2-formyl-5-benzyloxymethyl-4-pyrrolidinol의 합성

  • 전학림 (숭실대학교 자연과학대학 화학과) ;
  • 윤신숙 (강남대학교 교양학부) ;
  • 신영숙 (숭실대학교 자연과학대학 화학과) ;
  • 남정이 (숭실대학교 자연과학대학 화학과)
  • Published : 19970300
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Abstract

A precursor of bulgecinine, (4S,5R)-1-acetyl-2-formyl-5-benzyloxymethyl-4-pyrrolidinol (15) has been synthesized from diacetone-D-glucose. Barton deoxygenation, conversion to an L-sugar and displacement with $N_3^-$ at C-5, and one-pot reductive cyclization at C-2 produced (6R)-6-Ο-benzyloxymethyl-(3R)-3-methoxy-2-oxa-5-azabicyclo-[2,2,1]heptane(13), a key intermediate for bulgecinine. N-Acetylation and acid hydrolysis of 13 furnished a precursor of bulgecinine, (2S,4S,5R)-pyrrolidinol derivative 15 and its (2R,4S,5R)-diastereomer.

Bulgecinine의 선구물질인 (4S,5R)-1-acetyl-2-formyl-5-benzyloxymethyl-4-pyrrolidinol (15)을 diacetone-D-glucose로부터 합성하였다. Barton 탈산소화 반응, C-5에서의 반전, $-N_3$ 도입과 환원 및 C-2에서의 고리 형성을 통해 bulgecinine의 핵심 중간체인 두 고리 화합물 (6R)-6-Ο-benzyloxymethyl-(3R)-3-methoxy-2-oxa-5-azabicyclo-[2,2,1]heptane (13)을 합성하였다. 화합물 13을 N-아세틸화 후 산가수분해하여 얻은 bulgecinine 선구물질은 토토머화가 수반되어 (2S,4S,5R)-pyrrolidinol 유도체 15와 함께 (2S,4S,5R)-부분 입체 이성질체도 얻어졌다.

Keywords

References

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