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A new synthesis of (±)-myodesmone

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Abstract

(±)-Myodesmone was synthesized, starting from 2-cyclopentenone. The key reaction involved α-dimethoxymethylation of 2-cyclopentenone and organocopper conjugate addition reaction.

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References Cited

  • Blackburne, I. D., Park, R. J. and Sutherland, M. D., Terpenoid Chemistry XVIII. Myodesmone and Isomyodesmone, Toxic furanoid ketones fromMyoporum deserti andM. acuminatum.Aust. J. Chem., 24, 995–1007 (1971).

    CAS  Google Scholar 

  • Branca, J. and Smith, A. B., A Stereospecific total synthesis of (±)-Pentenomycin I, (±)-Pentenomycin II, and Dehydropentenomycin I. A versatile latent α-ketovinyl anion eqivalent.J. Am. Chem. Soc., 100, 7767–7768, (1978).

    Article  CAS  Google Scholar 

  • Corey, E. J. and Enders, D., Synthetic routes to polyfunctional molecules via metallated N,N-dimethyl-hydrazones.Tetrahedrone Lett., 11–14 (1976).

  • Dieter, R. K. and Dieter, J. W., Total Synthesis of (±)-Myodesmone employing a regiospecifically substituted α-oxoketone dithioacetal.J. Chem. Soc., Chem. Commun., 1378–1380 (1983).

  • Fadel, A., Yefsah, R. and Sala, N. J., Anhydrous iron(III) chloride dispersed on silica gel; III. A convenient and mild reagent for deacetalization in dry medium.Synthesis., 37–40 (1987).

  • Itoh, A., Ozawa, S., Oshima, K. and No, H., Aldol reaction of aluminium enolate resulting from 1,4-addition of Me2AlSPh to α,β-unsaturated carbonyl compound. A 1-acylethenyl anion equivalent.Tetrahedron Lett., 21, 361–364 (1980).

    Article  Google Scholar 

  • Kim, S., Kim, Y. G. and Park, J. H., A simple procedure for α-alkoxyalkylation of α,g-enones via pyridiniosilylation.Tetrahedron Lett., 52, 2043–2044 (1991).

    Article  Google Scholar 

  • Perrin, D. D., Armarego, L. F. and Perrin, O. R., Purification of laboratory chemicals 2nd ed., Pergamon Press, New York, 1980.

    Google Scholar 

  • Shono, T., Matsumura, Y., Kashimura, S. and Hatanaka, K., One step joining reaction of thiolate anions, activated olefins, and carbonyl compounds.J. Am. Chem. Soc., 101, 4752–4753 (1979).

    Article  CAS  Google Scholar 

  • Stork, G. and Benaim, J., Monoalkylation of α,β-unsaturated ketones via metalloenamines.J. Am. Chem. Soc., 93, 5938–5939 (1971).

    Article  CAS  Google Scholar 

  • Stork, G. and Maldonado, L., Anions of protected cyanohydrins as acyl carbanion equivalents and their use in a new synthesis of ketones.J. Am. Chem. Soc., 93, 5286–5287 (1971).

    Article  CAS  Google Scholar 

  • Stork, G. and Maldonado, L., Conjugate addition of acyl carbanion equivalents via the protected cyanohydrin method.J. Am. Chem. Soc., 96, 5272–5274 (1974).

    Article  CAS  Google Scholar 

  • Suzuki, M., Kawagishi, T. and Noyori, R., A new procedure for α-alkoxyalkylation of α,β-unsaturated ketones.Tetrahedron Lett., 22, 1809–1812 (1981).

    Article  CAS  Google Scholar 

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Park, O.S., Hwang, H.J. & Lee, W.Y. A new synthesis of (±)-myodesmone. Arch. Pharm. Res. 16, 205–208 (1993). https://doi.org/10.1007/BF02974483

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