Total Synthesis of 7,9-Dideoxydaunomycinone, Aglycone of Antitumor Antibiotic Daunorubicin (Ⅰ)

항암항생제 Daunorubicin의 Aglycone, 7,9-Dideoxydaunomycinone의 합성 (제1보)

  • In Ho Cho (Department of Chemistry, Chonbuk Univeristy) ;
  • Richard P. Rhee (Department of Chemistry, Chonbuk Univeristy) ;
  • Young Soy Rho (Department of Chemistry, Chonbuk Univeristy) ;
  • F. M. Hauser (Oregon Gradeate Center)
  • 조인호 (전북대학교 자연과학대학 화학과) ;
  • 이풍래 (전북대학교 자연과학대학 화학과) ;
  • 노영쇠 (전북대학교 자연과학대학 화학과) ;
  • Published : 1986.02.20

Abstract

7,9-Dideoxydaunomycinone (32), a late-stage precursor of the aglycone of antitumor antibiotic daunorubicin(2a) was prepared from 3-methoxybenzoic acid(5). Thus, 3-methoxybenzoic acid was converted to 4-methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone(11), which furnished trimethoxynaphthoate 16 upon ring annelation developed by Hauser and Rhee. The trimethoxynaphthoate 16 upon ring annelation developed by Hauser and Rbee. The trimethoxynaphtboate 16 was then transformed into phenylsulfonylnaphthofuranone 22, which was used to make anthracenoate 24 via Michael type reaction with 7-(ethylenedioxy)-2-octenoate(23). Conversion of anthracenoate 24 to tetracyclic product 28, followed by subsequent deprotection of the methyl groups in ring-B and C furnished 7, 9-Dideoxydaunomycinone(32).

Keywords

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