Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Total Synthesis of 6-Deoxybisanhydrodaunomycinone Anticancer Antibiotics

항암항생제 6-Deoxybisanhydrodaunomycinone의 합성

  • Cho, In Ho (Department of Chemistry, Chonbuk National University) ;
  • Rho Young Soy (Department of Chemistry, Chonbuk National University) ;
  • Park, Si Ho (Department of Chemistry, Chonbuk National University) ;
  • Ahn Koo Hyeon (Department of Chemistry, Chonbuk National University) ;
  • Sin Hong Sig (Department of Chemistry, Chonbuk National University) ;
  • Han Byoung Ku (Department of Chemistry, Chonbuk National University)
  • 조인호 (전북대학교 자연과학대학 화학과) ;
  • 노영쇠 (전북대학교 자연과학대학 화학과) ;
  • 박시호 (전북대학교 자연과학대학 화학과) ;
  • 안구현 (전북대학교 자연과학대학 화학과) ;
  • 신홍식 (전북대학교 자연과학대학 화학과) ;
  • 한병구 (전북대학교 자연과학대학 화학과)
  • Published : 1993.01.20
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Abstract

A brief route for total synthesis of 6-deoxybisanhydrodaunomycinone(20) was described, namely the precursor of the daunomycinone, the aglycone of the anticancer antibiotic daunorubicin (1b). The prepared enone 4 was condensed with phthalide sulfone 7 to afford anthraquinone 10 after oxidation and methylation. The benzylic group of 10 was brominated, and subsequent oxidation with bis(tetrabutylammonium) dichromate followed by cyclization give hydroxyanthraquinone 16, which was displaced with thiophenol. Oxidation of 17 with m-CPBA in phosphate buffer solution afforded anthraquinonyl sulfone 18 which was condensed with methyl vinyl ketone (19) to furnish 20.

항암항생제 Danuorubicin(1b)의 aglycone인 daunomycinone의 전이물질 6-deoxybisanhydrodaunomycinone(20)의 전 합성이 이루어졌다. 만들어진 enone 화합물 4를 phthalide sulfone 7과 반응시킨 뒤 oxidation과 methylation을 시켜서 anthraquinone 화합물 10을 얻었다. 화합물 10의 benzyl기를 bromination시켜서 얻은 monobromo 화합물 11을 bis(tetrabutylammonium) dichromate로 고리화반응을 시켜서 hydroxyanthraquinone 화합물 16을 얻은 뒤 OH기를 thiophenol로 치환시켰다. sulfide 화합물 17은 phosphate buffer 용액속에서 m-CPBA로써 산화시켜서 anthraquinonyl sulfone 화합물 18을 얻은 뒤 methyl vinyl ketone(19)과 결합시켜서 화합물 20을 얻었다.

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