Abstract
A new formal total synthesis of (+)-6-oxo-3,4,4a, 5-tetrahydro-3-hydroxy-2,2-dimethylnaphtho-1,2-pyran (1) which has been known to have bactericidal, bacteriostatic, fungicidal, fungistatic activities againstStaphylococcus aureus and other microorganism, is described. The key reaction involves enantioselective prenylation of α-tetralone via chiral lithioenamine.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References Cited
Brieskorn, C. H. and Poehlmann, R., The occurrence of isomeric catalponol and tectol dimethyl ether in the root ofLippia origanoides.Arch. Pharm., 309, 829–836 (1976).
Brown, H. C. and Krishnamurthy, S., 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.J. Am. Chem. Soc., 94, 7159–7161 (1972).
Chidambaram, N. and Chandrasekaram, S.,tert-Butyl Hydroperoxide-Pyridinium Dichromate: A Convenient Reagent System for Allylic and Benzylic Oxidations.J. Org. Chem., 52, 5048–5051 (1987).
Inoue, K., Inouye, H., Taga, T., Fujita, R., Osaki, K. and Kuriyama, K., Quinones and Related Compounds in Higher Plants. IX. Absolute Structures of Catalponol and Its Congeners.Chem. Pharm. Bull. 28(4), 1224–1229 (1980).
Macambira, L. M. A., Andrade, C. H. S., Matos, F. J. A. and Craveiro, A. A., Naphthoquinoids fromLippia sidoides.J. Nat. Pro., 49 (2), 310–312 (1986).
Meyers, A. I., William, D. R., Erickson, G. W., White, S. and Druelinger, M., Enantioselective Alkylation of Ketones via Chiral, Nonracemic Lithioenamines. An Asymmetric Synthesis of α-Alkyl and α,α-t'-Dialkyl Cyclic Ketones.J. Am. Chem. Soc., 103, 3081–3087 (1981).
Mitsui, S., Kasahara, A. and Hanaya, K., The stereochemistry of a tetralin-1-ols.Bull. Chem. Soc. Jpn., 41, 2523–2528 (1968).
Park, O. S. and Jang, B. S., Synthesis of 4-Hydroxycoumarin Derivatives-1: An Efficient Synthesis of Flocoumafen.Arch. Pharm. Res., 18, 277–281 (1995).
Perrin, D. D., Armarego, L. F. and Perrin, O. R.,Purification of laboratory chemicals. 2nd ed., Pergamon Press, New York, 1980.
Shadbolt, R. S., Woodward, D. R. and Birchwood, P. J., Synthesis of Some Tetrahydronaphthyl- and Flavanylcoumarins.J. Chem. Soc. Perkin., I, 1190–1194 (1976).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Park, O.S., Lim, J.G. 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. Arch. Pharm. Res. 19, 581–585 (1996). https://doi.org/10.1007/BF02986032
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02986032