Total Synthesis of 11-Deoxy-$\beta$-rhodomycinone Antitumor Antibiotics

항암항생제 11-Deoxy-$\beta$-rhodomycinone의 합성

  • 노영쇠 (전북대학교 자연과학대학 화학과) ;
  • 강혼수 (미원중앙연구소 제3연구실) ;
  • 신홍식 (전북대학교 자연과학대학 화학과)
  • Published : 1993.12.01

Abstract

Methyl 3-[(phenylsulfonyl)methyl]-1, 4, 8-trimethoxy-2-naphthoate(7) preparad by 3 steps was condensed with 5-ethyl-2-cyclohexen-1-one(8) to afford the teracyclic aromatic ring system compound 10, which was stepwise converted into the precursor of 11-Deoxy-$\beta$-rhodomycinone by means of various functional groups transformation.

Keywords

References

  1. Doxorubicin, Anticancer Antiviotics Arcamone,F.
  2. Anthracyclines, Current Status and Developments Crooke,S.T.;Reich,S.D.
  3. The Chemistry of Antitumor Antibiotics Remers,W.R.
  4. Chronicles of Drug Discovery v.2 Arcamone,F.;Bindra,J.S.(ed.);Ledinicer,D.(ed.)
  5. Tetrahedron Lett. v.31 Anthracyclinones, Part Ⅶ. For part Ⅵ Bertounesque,E.;Florent,J.C.;Monneret,C.
  6. J. Am. Chem. Soc. v.102 Structures of Novel Anthracycline Antitumor Antibiotics from Micromonospora Peucetica Arcamone,F.;Cassinelli,G.;DiMatteo,F.;Forenza,S.;Ripamonti,M.C.;Rivola,G.;Vigenvani,A.;Clardy,J.;McCabe,T.
  7. Drugs Exp. Clin. Res. v.11 Tone,H.;Nishida,H.;Takeuchi,T.;Umezawa,H.
  8. Carr. Chemother. Immunother. Proc. Int. Congr. Chemother., 13th. Tone,H.;Takeuchi,T.;Umezawa,H.
  9. Synthesus v.521 An Improved Synthesis of Benzo-and Naphthoquinones from Hydroquinone Dimethl Ethers Syper,L.;Kloc,K.;Mlochowski,J.;Szulc,Z.
  10. J. Org. Chem. v.43 New Synthetic Methids for the Regioselective Annelation of Aromatic Ring Hauser,F.M.;Rhee,R.P.
  11. J. Org. Chem. v.54 1(4H)-Naphthalenones in Anthracyclinone Synthesis: A New Route for the Total Synthesis of(+/-)-Aklavinone Hauser,F.M.;Hewawasam,P.;Rho,Y.S.
  12. J. Kor. Chem. Soc. v.37 Total Synthesis of 6-Deoxybisanhydrodaunomycinone Anticacer Antibitics Rho,Y.S.;Cho,I.H.;Park,S.H.;Ahn,K.H.;Sin,H.S.;Han,B.K.
  13. J. Kor. Chem. Soc. v.36 Total Synthesis of 9,10-Dideoxy-β-rhodomycinone Rho,Y.S.;Cho,I.H.;Sho,S.M.;Yoo,D.J.;Lee,J.Y.;Han,B.K.
  14. J. Org. Chem. v.57 Synthesis of Inhibitors of 2,3-Oxidosqualene-lanos terol Cyclase Dodd,D.S.;Oelshlager,A.C.
  15. J. Org. Chem. v.41 Facile Reduction of Alkyl Tosylates with Lithium Triethylborohydride. An Advantageous Procedure for Deoxygenation of Cyclic and Acyclic Alcohols Krishnamurthy,S.;Brown,H.C.
  16. J. Kor. Chem. Soc. v.30 Total Synthesis of 7,9-Dideoxydaunomycinone Rho,Y.S.;Cho,I.H.;Rhee,R.P.
  17. J. Org. Chem. v.38 α-Halocarbonyl Compounds. Ⅱ. A Position Specific Preparation of α-Bromo Ketones by Bromination of Lithium Enolates Stotter,P.L.;Hill,K.A.
  18. J. Am. Chem. Soc. v.98 New Synthetic Reactions. Sulfenylations and Dehydrosulfenylations of Esters and Ketones Trost,B.M.;Salzmann,T.N.;Hiroi,K.
  19. Tetrahedron v.22 A General Route for Total Synthesis of 9-Alkyl-9-hydroxy Aklavinoes and Pyrromycinones Hauser,F.M.;Prasanna,D.
  20. J. Kor. Chem. Soc. v.32 Synthesis of (+/-)-γ-Rhodomycinone and 10-Deoxy-γ-rhodomycinone Rho,Y.S.;Cho,I.H.;Chung,J.S.;Rhee,R.P.
  21. Tetrahedron v.40 Synthesis of the Feudomycinone and Rhodomycinone Krohn,K.;Priyone,W.
  22. Tetrahedron Lett. v.21 Boron Trihalide-Methyl Sulfide Complexes as Convenient Reagents for Dealkylation of Aryl Ether Williard,P.G.;Fryhle,C.B.