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

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.

Keywords

References

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