Abstract
trans-Ethyl 1,2,3,4a,5,6,8a-octahydro-2-benzyl-4-hydroxy-6-methyl-5-isoquinoline-carboxylate was prepared by intramolecular Diels-Alder reaction as a precursor of newly designed aza-analogue of mevinolin.
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Alberts, A. W., Chen, J., Kuron, G., Hunt, V., Huff, J., Hoffman, C., Rothrock, J., Lopez, M., Joshua, H., Harris, E., Patchett, A., Monaghan, R., Currie, S., Stapley, E., Albers-Schonberg, G., Hensens, O., Hirshfield, J., Hoogsteen, K., Liesch, J., and Springer, J., Mevinolin: a highly potent competitive inhibitor of hydroxyme-thylglutaryl-coenzyme A reductase and cholesterol lowring agents.Proc. Natl. Acad. Sci., U.S.A., 77, 3957–3961 (1980).
Borch, R. F., Reductive aminatuion with sodium cyanoborohydride.Org. Syn., 52, 124–127 (1972).
Brown, A. G., Smale, T. C., King, T. J., Hasenkamp, R. and Thompson, R. H., Crystal and molecular structure, a new antifungal metabolite fromPenicillium brevicompactum.J. Chem. Soc., Perkin Trans I, 1165–1170 (1976).
Endo, A., Kuroda, M., and Tsujita, Y., ML-236A and ML-236B, new inhibitors of cholestereogenesis produced byPenicillium citrinum.J. Antibiotics, 29, 13 46–1348 (1976).
Endo, A., Monacolin K, a new hypocholesterolemic agent produced by a monascus species.J. Antibiotics, 32, 852–854 (1979).
Grundy, S. M., HMG-CoA reductase inhibitors for treatment of hypercholesterolemia.New Engl. J. Med., 319, 24–32 (1988).
Heathcock, C. H., Davis, B. R., and Hadley, C. R., Synthesis and bilogical evaluation of a monocyclic, fully functional analogue of compactin.J. Med. Chem., 32, 197–202 (1989).
Jahng, Y., and Kim, J.-I., The reaction of (E)-2,4-pentadienoic acid with aqueous bromine.Arch. Pharm. Res., 12, 229–230 (1989).
Kathawala, F. G., HMG-CoA reductase inhibitors: an exciting development in the treatment of hyperlipidemia.Med. Res. Rev., 11, 121–146 (1991).
Kim, J.-I., Ph. D. dissertation, Yeungnam University, August, 1993. Although one more stereoisomer is possible, it was not detectable in 300 MHz1H NMR spectrum.
Martin, S. F., Williamson, S. A., Gist, R. P., and Smith, K. M., Aspects of the intramolecular Diels-Alder reactions of some 1,3,9-trienoic amides, amines, and esters.J. Org. Chem., 48, 5170–5180 (1983).
Roush, W. R., and Hall, S. E., Studies on the total synthesis of chlorothricolide.J. Am. Chem. Soc., 103, 5200–5211 (1981).
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Jahng, Y., Kim, JI. Aza-analogue of mevinolin: Synthesis of substituted octahydroisoquinoline, the bottom half of aza-analogue of mevinolin. Arch. Pharm. Res. 17, 104–108 (1994). https://doi.org/10.1007/BF02974232
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DOI: https://doi.org/10.1007/BF02974232