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The Pharmaceutical Society of Korea (대한약학회)
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Studies on the Synthesis of Naphthoquinoids-1 : Formal Total Synthesis of (+)-6-Oxo-3,4,4a,5-tetra hydro-3-hydroxy-2,2-dimethylnaphtho-1,2-pyran

  • Park, Oee-Sook (Department of Chemistry, Chungbuk National University) ;
  • Lim, Jae-Gyeong (Department of Chemistry, Chungbuk National University)
  • Published : 1996.12.01
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Abstract

A new formal total synthesis of (+)-6-oxo-3, 4, 4a, 5-tetrahydro-3-hydroxy-2, 2-dimenthylnaphtho-1, 2-pyran (1) which has been known to have bactericidal, bacteriostatic, fungicidal, fungistatic activities against Staphylococcus aureus and other microorganism, is described. The key reaction involves enantioselective prenylation of .alpha.-tetralone via chiral lithioenamine.

Keywords

References

  1. Arch. Pharm. v.309 The occurrence of isomeric catalponol and tectol dimethyl ether in the root of Lippia origanoides Brieskorn,C.H.;Poehlmann,R.
  2. J. Am. Chem. Soc. v.94 Lithium Tri-sec-butylborohydride. A New Reagent for the Reduction of Cyclic and Bicyclic Ketones with Super Stereoselectivity. A Remarkably Simple and Practical Procedure for the Conversion of Ketones to Alcohols in Exceptionally High Stereochemical Purity Brown,H.C.;Krishnamurthy,S.
  3. J. Org. Chem. v.52 Tert-Butyl Hydroperoxide-Pyridinium Dichromate: A Convenient Reagent System for Allylic and Benzylic Oxidations Chidambaram,N.;Chandrasekaram,S.
  4. Chem. Pharm. Bull. v.28 no.4 Quinones and Related Compounds in Higher Plats. Ⅸ. Absolute Structure of Catalponol and Its Congeners Inoue,K.;Inouye,H.;Taga,T;Fujita,R.;Osaki,K.;Kuriyama,K.
  5. J. Nat. Pro. v.49 no.2 Naphthoquinoids from Lippia Sidoides Macambira,L.M.A.;Andrade,C.H.S.;Matos,F.J.A.;Craveiro,A.A.
  6. J. Am. Chem. Soc. v.103 Enantioselective Alkylation of Ketones via Chiral, Nonracemic Lithioenamines. An Asymmetric Synthesis of α-Alkyl and α,α'-Dialkyl Cyclic Ketones Meyers,A.I.;William,D.R.;Erickson,G.W.;White,S.;Druelinger,M.
  7. Bull. Chem. Soc. Jpn. v.41 The stereo-chemistry of a tetralin-1-ols Mitsui,S.;Kasahara,A.;Hanaya,K.
  8. Arch. Pharm. Res. v.18 Synthesis of 4-Hydroxycoumarin Derivatives-1: An Efficient Synthesis of Flocoumafen Park,O.S.;Jang,B.S.
  9. Purification of laboratory chemicals(2nd ed.) Perrin,D.D.;Armarego,L.F.;Perrin,O.R.
  10. J. Chem. Soc. Perkin. v.I Synthesis of Some Tetrahydronaphthyl- and Flavanylcoumarins Shadbolt,R.S.;Woodward,D.R.;Birchwood,P.J.