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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 18
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Original Articles

Synthesis of Resorcinols via a Michael Addition-Dieckman Cyclization Sequence of Dimethyl 1,3-Acetonedicarboxylate Anion with Alkyl Alkynoates

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Pages 3461-3469 | Received 06 Apr 1998, Published online: 22 Aug 2006

References

  • Bamfield , P. and Gordon , P. F. 1984 . Chem. Soc. Rev. , 13 : 441 Review:
  • Ghera , E. and Ben-David , Y. 1988 . J. Org. Chem. , 53 : 2972
  • Itoh , Y. , Brossi , A. , Hame , E. and Lin , C. M. 1988 . Helv. Chim. Acta , 71 : 1199
  • Ozaki , Y. , Mochida , K. and Kim , S. 1987 . Chem. Pharm. Bull. , 35 : 1790
  • Ozaki , Y. and Kim , S. 1989 . Chem. Pharm. Bull. , 37 : 304
  • Ozaki , Y. , Mochida , K. and Kim , S. 1989 . J. Chem. Soc., Perkin Trans. I , : 1219
  • Ingam , J. L. 1983 . Progress in the Chemistry of Organic Natural Products. , Edited by: Herz , W. , Grisoebach , H. and Kirby , G. W. Vol. 43 , 1 – 266 . Vienna, New York : Springer-Verlag .
  • Bergmann , E. D. , Ginsburg , D. and Pappo , R. 1959 . Org. React. , 10 : 179
  • Schaefer , J. P. and Bloomfield , J. J. 1967 . Org. React. , 15 : 1
  • Patent, D. O. S., 2 359 410 . 1973 .
  • Deuschel , W. 1951 . Helv. Chim. Acta , 34 : 168
  • Ried , W. and König , E. 1973 . Liebigs Ann. , 757 : 153
  • Covarrubias-Zúñiga , A. and Ríos-Barrios , E. 1997 . J. Org. Chem. , 62 : 5688
  • After the present paper was written, we found that diminishing the acidic character of the second proton participating in this process (by the introduction of an allylic group in dimethyl 1,3-acetonedicarboxylate), we obtained the resorcinol 7 from the kinetic enolate in 28% yield and the diastereoisomeric alcohols 8 from the thermodynamic enolate in 63% yield, using 4-pivaloyloxy-2-butynal as Michael acceptor.7
  • Nicolaou , K. C. and Webber , S. E. 1986 . Synthesis , : 453
  • Frazer , M. M. and Raphael , R. A. 1955 . J. Chem. Soc. , : 4280
  • Bowden , K. , Heilbron , I. M. , Jones , E. R. H. and Weedon , B. C. L. 1946 . J. Chem. Soc. , : 39
  • Black , T. H. 1983 . Aldrichimica Acta , 16 : 3
  • Earl , R. A. and Towsend , L. B. 1981 . Org. Synth. , 60 : 8
  • Brandsma , L. 1988 . Preparative Acetylenic Chemistry , 101 New York : Elsevier .
  • Venkataraman , G. 1951 . Pr. Indian Acad. [A] , 34 : 368 – 377 .

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