Abstract
6,10,14,18-Tetramethyl-5,9,13,17(E,E,E)-nonadecatetraen-2-one was synthesized from geraniol or 6-methyl-5(E)-hepten-2-one in 6 steps, respectively. The key step in both syntheses, was the condensation of phenyl sulfone compound and allylic chloride.
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Collington, E. W. and Meyers, A. I., A facile and specipic conversion of allylic alcohols to allylic chlorides without rearrangement.J. Org. Chem., 36, 3044–3345 (1971).
Corey, E. J., Katzenellenbogen, J. K. and Posner, G. H., A new stereospecific synthesis of trisubstituted olefines. Stereospecific synthesis of farnesol.J. Am. Chem. Soc., 89, 4245–4247 (1967).
Isler, O. and Doebel, K., Synthesis in the vitamine K series (I) vitamine K1.Helv. Chim. Acta, 37, 225–233 (1954).
Kimel, W., Surmatis, J. D., Weber, J., Chase, G. O., Sax, N. W. and Ofener, A., Synthesis of pseudoionone homologs and related compounds.J. Org. Chem., 22, 1611–1618 (1957).
Meinwald, J. and Opheim, K., Chemical defense mechanism of arthropods. Stereospecific synthesis of Gyrinidal, norsesquiterpenoid aldehyde from Gyrinid beetles.Tetrahedron Letters, 281–284 (1973).
Murakami, M., Oketani, K., Fujisaki, H., Wakabayashi, T., Inai, Y., Abe, S., Yamatsu, I. and Ohgo, T., Effect of synthetic acyclic polyisoprenoids on the cold-rest-raint stress induced gastric ulcer in rats.Jpn. J. Pharmacol., 33, 549–556 (1983).
Obol’nikova, E. A., Yanotovskii, M. T. and Samokhvalov, G. L., Synthetic studies of polyene compounds XXIII. Synthesis of diisoprenoid oxo alcohol, 4-methyl-4-nonen-1-ol-8-one by Wittig reaction.Zh. Obsheh. Khim., 34, 3975–3979 (1964).
Perrin, D. D., Armarego, L. F. and Perrin, O. R.,Purification of laboratory chemicals 2nd ed., Pergamon Press, New York, 1980.
Sato, K., Iroue, S. and Ota, S., The synthesis of isoprenoid ketones.J. Org. Chem., 35, 565–566 (1970).
Trost, B. M., Arndt, H. C., Strege, P. E. and Verhoeven, T. R., Desulfonylation of aryl alkyl sulfones.Tetrahedron Letters, 39, 3477–3478 (1976).
Trost, B. M., Weber, L., Strege, P. and Fullerton, T. J. and Dietsche, T. J., Allylic alkylation: Nature of the nucleophile and application to prenylation.J. Am. Chem. Soc., 100, 3426–3434 (1976).
Trost, B. M., Weber, L., Strege, P. and Fullerton, T. J. and Dietsche, T. J., Allylic alkylation: Nature of the nucleophile and application to prenylation.J. Am. Chem. Soc., 100, 3426–3434 (1978).
Umbreit, M. A. and Sharpless, K. B., Allylic oxidation of olefins by catalytic and stoichiometric selenium dioxide with tert-butylhydroperoxide.J. Am. Chem. Soc., 99, 5526–5528 (1977).
Yamatsu, I., Abe, S., Inai, Y., Suzuki, T., Kinoshita, K., Mishima, M., Katoh, Y., Kobayaski, S., Murakami, M. and Yamada, K., Agent for improving hepatic function.Ger. Offen. DE 3,226,687 (1983).
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Park, O.S., Ahn, S.K. A new synthesis of 6,10,14,18-Tetramethyl-5,9,13,17 (E,E,E)-nonadecatetraen-2-one. Arch. Pharm. Res. 16, 265–270 (1993). https://doi.org/10.1007/BF02977514
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DOI: https://doi.org/10.1007/BF02977514