Abstract
The Diels-Alder reaction of lambertianic acid with maleic anhydride occurred in a stereoselective fashion and yielded diastereoisomeric (1R,2S,6R,7R)- and (1S,2R,6S,7S)-exo-adducts. The latter reacted with L-valinol to give the corresponding diterpenoid imides, 4-aza-9-oxabicyclo[2.2.1]dec-8-enes. Reactions of lambertianic acid with N-substituted maleimides in the presence of Lewis acids afforded diastereoisomeric adducts having both exo and endo configuration. Some transformations of the adducts were examined with a view to obtain cantharidin and dihydroisoindole analogs.
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REFERENCES
Chernov, S.V., Shul'ts, E.E., Shakirov, M.M., and Tolstikov, G.A., Russ. J. Org. Chem., 2002, vol. 38, p. 665.
Yosef, R., Carrel, J.E., and Eisner, T., J. Chem. Ecol., 1996, vol. 22, p. 173.
Dauben, V.G., Lam, J.Y.L., and Guo, Z.R., J. Org. Chem., 1996, vol. 61, p. 4816.
Li, Y.-M. and Casidaa, J.E., Proc. Natl. Acad. Sci. USA, 1992, vol. 89, p. 11 867.
Guba, P.K., Poi, R., and Bhattacharyya, A., Phytochemistry, 1990, vol. 29, p. 2047.
Vogel, P., Cossy, J., Plumet, J., and Arjona, O., Tetrahedron, 1999, vol. 55, p. 13 521.
Lin, P-Y., Shi, S.-J., and Hsu, F.-L., Synth. Commun., 1999, vol. 29, p. 1611.
McCluskey, A., Bowyer, M.C., Collins, E., Sim, A.T.R., Sakoff, J.A., and Baldwin, M.L., Bioorg. Med. Chem. Lett., 2000, vol. 10, p. 1687.
Raldugin, V.A., Zubtsova, L.M., and Shmakova, L.M., Khim. Prirod. Soedin., 1983, no. 1, p. 112.
Gill, G.B., James, G.D., Oates, K.V., and Pattenden, G., J. Chem. Soc., Perkin Trans. 1, 1993, no. 11, p. 2567.
Braish, T.F. and Fox, D.E., Synlett, 1992, no. 12, p. 979.
Buinova, E.F., Solntsev, A.N., and Volozhin, A.I., Izv. Akad. Navuk Belarusi, 1996, no. 4, p. 118.
Zhao, Q., Zou, C., Hao, X.J., and Chen, Y.Z., Chin. Chem. Lett., 1999, vol. 10, p. 531.
Corey, E.J. and Shimoji, K., Tetrahedron Lett., 1983, vol. 24, p. 169.
Meyers, A.I., Dickman, D.A., and Bailey, T.R., J. Am. Chem. Soc., 1985, vol. 107, p. 7974.
Hromatka, O., Sengstschmid, G., and Eichinger, K., Monatsh. Chem., 1971 vol 102, p. 1015.
Rich D.H., Gesellchen, P.D., Tong, A., Cheung, A., and Buckner, C.K., J. Med. Chem., 1975, vol. 18, p. 1004.
Knock, F.E., US Patent no. 337 584, 1967; Chem. Abstr., 1968, vol. 68, p. 77 793.
Igarashi, Y., Yagami, K., and Nakayoshi, C., JPN Patent no 23–8326, 1990; Chem. Abstr., 1992, vol. 117, no. 145 299.
Otsu, T., Matsumoto, A., Kubota, T., and Mori, S., Polym. Bull., 1990, vol. 23, p. 43; Chem. Abstr., 1990, vol. 112, no. 235 932.
Giezelrich, H. and Duschner, C. Chem. Ber., 1896, vol. 29, p. 2062.
Keller, O. and Rudinger, J., Helv. Chim. Acta, 1975, vol. 58, p. 531.
Obshchii praktikum po organicheskoi khimii (General Practicum on Organic Chemistry), Kost, A.N., Ed., Moscow: Mir, 1965, p. 532.
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Kharitonov, Y.V., Shul'ts, E.E., Shakirov, M.M. et al. Synthetic Transformations of Higher Terpenoids: VIII. [4+2]-Cycloaddition Reactions of Lambertianic Acid. Russian Journal of Organic Chemistry 39, 57–74 (2003). https://doi.org/10.1023/A:1023490528591
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DOI: https://doi.org/10.1023/A:1023490528591