Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Total Synthesis of 9,10-Dideoxy-${\beta}$-rhodomycinone

9,10-Dideoxy-${\beta}$-rhodomycinone의 합성

  • In Ho Cho (Department of Chemistry, Chonbuk National University) ;
  • Young Soy Rho (Department of Chemistry, Chonbuk National University) ;
  • Sang Moon Sho (Department of Chemistry, Chonbuk National University) ;
  • Dong Jin Yoo (Department of Chemistry, Chonbuk National University) ;
  • Jun Yong Lee (Department of Chemistry, Chonbuk National University) ;
  • Byoung Ku Han (Department of Chemistry, Chonbuk National University)
  • 조인호 (전북대학교 자연과학대학 화학과) ;
  • 노영쇠 (전북대학교 자연과학대학 화학과) ;
  • 소상문 (전북대학교 자연과학대학 화학과) ;
  • 유동진 (전북대학교 자연과학대학 화학과) ;
  • 이준용 (전북대학교 자연과학대학 화학과) ;
  • 한병구 (전북대학교 자연과학대학 화학과)
  • Published : 1992.12.20
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Abstract

Total synthesis of 9,10-dideoxyrhodomycinone(30) which is the late-stage precursor of naturally occuring ${\beta}$-rhodomycinone(1) is described. After phthalide sulfone 4 was converted to naphthalide sulfone 12 by the several step. Michale addition of naphthalide sulfone 12 which was converted to an anion with 5-ethyl-1,3-cyclohexenone(21) gave a good yield of linearly condensed tetracyclic ketone compound 26. The keto group of 26 was reduced with sodium borohydride and protected by methyl group to afford compound 28. 9,10-Dideoxy-${\beta}$-rhodomycinone(30) was synthesized from pentamethoxy tetracyclic compound 28 by oxidative demethylation and demethylation of 29.

${\beta}$-rhodomycinone(1)의 전 단계물질인 9,10-dideoxyrhodomycinone(30)의 전 합성이 이루어졌다. Phthalide sulfone 4를 몇 단계의 반응을 진행시켜서 naphthalide sulfone 12로 변형시킨 뒤, 음이온으로 변형된 naphthalide sulfone 12를 5-ethyl-1,3-cyclohexenone(21)과 Michael 부가반응시켜서 선형으로 결합된 tetracyclic 케톤 화합물 26을 좋은 수율로 얻었다. 화합물 26의 케톤기는 sodium borohydride로 환원시키고 메틸기로 보호하여 화합물 28을 얻었다. 9,10-Dideoxy-${\beta}$-rhodomycinone(30)은 pentamethoxy tetracyclic 화합물 28을 oxidative demethylation시키고 메틸기를 제거시켜서 합성하였다.

Keywords

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