Oxidation of o-Isopropylphenol with Lead Tetraacetate: Synthesis of the Unit of Celastroidin Terpenes by the Diels-Alder Condensation

• Autorzy: Jankowski C. , Savoie A. , Lesage D. , Boivin D. , Leclair G. , Diaz T. E. , Reyes-Chilpa R. , Jimenez-Estrada M. , Barrios H.
• Języki publikacji: EN

Abstrakty

EN

Lead tetraacetate oxidation of o-isopropyl phenol under various conditions led to the dienone acetate which, when dimerized, represents a central part of the celastroidin penta- and hexa-terpenes (natural products from the Mexican shrub Hippocratea Celastroides). Six oxidation products formed in this reaction (the iso-propyl dienolone acetate, two dimers, benzoquinone, and two phenol acetates) were identified with help of 2D and 3D NMR, GC and LC-MS. From this, we concluded that the dimer skeleton observed for the dienolone acetate in natural products corresponded to the product from the photochemical pathway, and that the synthetic dimer has the opposite geometry; this was verified by molecular modelling. The oxidation of the second compound, o-cresol, leads to a similar profile of products.

Słowa kluczowe

EN

Diels-Alder on dienones; phenol Wessely oxidation; Diels-Alder in plant; Hippocratea dimeric diterpenes

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 2
• Strony: 429--440
• Opis fizyczny: Bibliogr. poz. 19, rys.

Twórcy

autor

Jankowski C.

• Département de chimie et biochimie, Université de Moncton, Moncton, NB, E1A 3E9, Canada

autor

Savoie A.

• Département de chimie et biochimie, Université de Moncton, Moncton, NB, E1A 3E9, Canada

autor

Lesage D.

• Département de chimie et biochimie, Université de Moncton, Moncton, NB, E1A 3E9, Canada

autor

Boivin D.

• Département de chimie et biochimie, Université de Moncton, Moncton, NB, E1A 3E9, Canada

autor

Leclair G.

• Département de chimie et biochimie, Université de Moncton, Moncton, NB, E1A 3E9, Canada

autor

Diaz T. E.

• Instituto de Quimica, UNAM, Cd Universitaria, Circuito Exterior, 04510 Mexico, DF, Mexico

autor

Reyes-Chilpa R.

• Instituto de Quimica, UNAM, Cd Universitaria, Circuito Exterior, 04510 Mexico, DF, Mexico

autor

Jimenez-Estrada M.

• Instituto de Quimica, UNAM, Cd Universitaria, Circuito Exterior, 04510 Mexico, DF, Mexico

autor

Barrios H.

• Instituto de Quimica, UNAM, Cd Universitaria, Circuito Exterior, 04510 Mexico, DF, Mexico

Bibliografia

• 1. Jimenez-Estrada M., Reyes-Chilpa R., Hernandez-Ortega S., Cristobal-Telésforo E., Torres-Colin L., Jankowski C.K., Aurmelas A. and Van Calsteren M.R.,Can .J Chem., 78, 248 (2000).
• 2. Oikawa H., Katayama K., Suzuki Y. and Ichihara A., .J Chem Soc. Chem. Comm., 1321 (1995); Barton D.H.R., Nakanishi K. and Meth-Cohn D., Comprehensive natural products chemistry. Vol. 1, 1999, pp. 367-408; Katayama K., Kobayashi T., Oikawa H., Honma M. and Ichihara A., Biochim. Biophys. Aeta, 1384, 387 (1998); Hano Y., Nomura T. and Ueda S., .J. Chem. Soc. Chem. Commm, 610 (1990); Cane D.E. and Guanglin L., .J Am. Chem. Soc., 117, 6633 (1995); Witter D.J. and Vedaras J.C., .1. Org. Chem., 61, 2613 (1996); Oikawa H., Kobayashi T., Katayama K., Suzuki Y. and Ichihara A., .J. Org. Chem., 63, 8748 (1998); Oikawa H., Yokota T., Abe T., Ichihara A., Sakamora S., Yoshizawa Y. and Vedeyas J.C., .J. Chem. Soc. Chem. Cammun., 1282 (1989); Laschat S.,Angew. Chem. Int. Ed. Engl., 35 (3), 289 (1996).
• 3. Matsumoto T., Ohsuga Y., Harada S. and Fukui K., Bull. Chem. Soc. Japan, 50 (1), 266 (1997); King F.E., King T.J. and Topliss J.G,. J. Chem. Soc., 573 (1957); Mori K. and Matsui M., Tetrahedron, 26, 3467 (1970); Matsumoto T., Tachibana Y., Uchida J . and Fukui K., Bull. Chem. Soc. Japan, 44, 2766 (1971); Tamai Y., Hagiwara H. and Uda H., .J. Chem. Soc. Perkin I, 1311 (1986); Mori K. and Matsui M., Tetrahedron, 24, 6573 (1968).
• 4. Bhaare N.K., Granger T., Macas T.S. and Yates P., .J. Chem. Soc. Chem. Cammun., 739 (1990); Macas T.S. and Yates P., Tetrahedron Lett., 24 (2), 147 (1983); Bhamare N.K., Granger T., John C.R. and Yates P., Tetrahedron Lett., 32 (35), 4439 (1991); Maeas T.S. and Yates P., Can. .J. Chem., 66, 1 (1987); Takaes F., Monatsh. Chem. , 95, 961 (1964);Zbiral F., Takacs F. and Wessely F., Monatsh. Chem., 95, 407 (1964).
• 5. Barton D.H., Magnus P.D. and Quinney J.C., .J. Chem. Soc. Perkin I, 1610 (1976).
• 6. Nicolaou K.C., Vassilikogiannakis G., Simonsen K.B., Baran P.S., Zhong Yong-Li, Vidali V.P., Pitsinos E.N. and Couladounes E.A., .J. Am. Chem. Soc., 122, 3071 (2000).
• 7. Shider B.B. and Shi Zgong-ping, .J. Org. Chem., 55, 5669 (1990); Quinker G, Billhardt U-M., Jakob H., Fischer G, Glenneberg J., Nagler P., Autze V., Helm N., Wacker M., Schwalbe T., Kurth Y., Bats J.W., Dumer G., Zimrnennann G. and Kessler H., Helv. Chim. Acta, 70, 771 (1987); Oikawa H., Katayama K., Suzuki Y. and 1chihalaA.,.J. Chem. Soc. Chem. Cammun., 1321 (1995).
• 8. Burgstahler A. and Worden L.R., .J. Am. Chem. S0c., 83, 2587 (1961).
• 9. Barton D.H., Magnus P. and Rosenfeld M.N.., .J. Chem. Soc. Chem. Cammun., 301 (1975); Barton D.H., Brewster A.G., Lay S.V., Read C.M. and Rosenfeld M.N., .J. Chem. Soc. Perkin I, 1473 (1981); Adler E. and Holrnberg K., Acta Chem. Scand., B28, 465 (1974).
• 10. Nicolaou K.C., Jautelat R., Vassilikogiannakis G., Baran P.S. and Simonsen K.B., Chem. Eur: .1., 5, 3651 (1999); Nicolaou K.C., Simonsen K.B., Vassilikogiannakis G., Baran P.S., Vidali V., Pitsinos E.N. and Couladoures E.A., Angew. Chem. Int. Ed., 38, 3555 (1999).
• 11.Abe N., Murata T. and Hirota A., Biosci. Biotechnol. Biochem., 65, 2120 (1998).
• 12. Savoie A., Thesis 4096, U de Moncton (2002); Natoli M., Nicolosi G. and Piattelli M., Tetrahedron Lett. ,31, 7371 (1990).
• 13. Cambie R.C., Higgs P.I., Read C.M., Rutledge P., Ryan G.R. and Woodgate P.D.,Austr: .J Chem., 43 (4), 681 ( 1990); Mori K. and Matsui M., Tetrahedron, 22, 879 (1966).
• 14. Cambie RC. and Franich R.A., Aust. .J Chem., 23, 93 (1970); Cambie R.C. and Denny W.A., Aust. .J. Chem., 22, 1699 (1969); Cambie R.C. and Franich R.A., Aust. .J. Chem., 24, 117 (1971); Kupchan S.M., Karim A. and Mareks C., .J. Org. Chem., 34, 3912 (1969); Trifonov L.S., Dreiding A.S., Hoeseh L. and Rast D.M., Helu Chim. Acta, 64, 1843 (1981).
• 15. Barton D.H., Magnus P. and Rosenfeld M.N., .J Chem. Soc. Chem. Cammun., 301 (1975).
• 16.Andrale R., Ayet W.A. and Mebe P.P., Can. J. Chem., 72, 2526 (1997); Andrale R., Aye Trifonov L.S., Can. J Chem., 74, 372 (1996); Banes-Seaman D. and Corey E. J., Org. Lem (1999).
• 17. Hyperchem 6 Mm‘ (U dc Moncton).
• 18. Rafel S., Cabarrocas G., Ventura M. and Perella T.,J. Chem. Soc. Perkins, 3837 (1998); Hera: M., Rafel S., Ventura M., Font J. and Ortuno R.M., Angew. Chem. Int. Ed, 92, 233 (1966).
• 19. Wagner B., Stojanovic N., Leclair G. and Jankowski C.K., J. Incl. Phenom. Macro. Che: (2003).