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Volumn 24, Issue 2, 2010, Pages 177-196

Different pathways for the deoxygenation of the A-ring of natural triterpene compounds

Author keywords

Deoxygenation; Maslinic acid; Oleanolic acid; Triterpene

Indexed keywords

CARBON; CARBONYL DERIVATIVE; ETHYLENE OXIDE; HYDROXYL GROUP; MASLINIC ACID; OLEANOLIC ACID; REAGENT; TOLUENESULFONIC ACID DERIVATIVE; TRITERPENE DERIVATIVE; XANTHINE DERIVATIVE;

EID: 75349089081     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786410903172098     Document Type: Article
Times cited : (9)

References (35)
  • 1
    • 0002541971 scopus 로고    scopus 로고
    • First diastereoselective synthesis of (-)-thyrsiflorin A methyl ester
    • Abad, A., Agullo, C., Arno, M., Marin, M.L., & Zaragoza, R.J. (1997). First diastereoselective synthesis of (-)-thyrsiflorin A methyl ester. Synlett, 574-576.
    • (1997) Synlett , pp. 574-576
    • Abad, A.1    Agullo, C.2    Arno, M.3    Marin, M.L.4    Zaragoza, R.J.5
  • 2
    • 0026738595 scopus 로고
    • The invention of radical reactions. Part XXIV. Relative rates of acylation and radical deoxygenation of secondary alcohols
    • Barton, D.H.R., Dorchak, J., & Jaszberenyi, J.Cs. (1992b). The invention of radical reactions. Part XXIV. Relative rates of acylation and radical deoxygenation of secondary alcohols. Tetrahedron, 48, 7435-7446.
    • (1992) Tetrahedron , vol.48 , pp. 7435-7446
    • Barton, D.H.R.1    Dorchak, J.2    Jaszberenyi, J.Cs.3
  • 4
    • 84918694212 scopus 로고
    • Radical deoxygenation of secondary and primary alcohols with phenylsilane
    • Barton, D.H.R., Jang, D.O., & Jaszberenyi, J.Cs. (1991b). Radical deoxygenation of secondary and primary alcohols with phenylsilane. Synlett, 435-438.
    • (1991) Synlett , pp. 435-438
    • Barton, D.H.R.1    Jang, D.O.2    Jaszberenyi, J.Cs.3
  • 5
    • 0025984290 scopus 로고
    • Radical deoxygenation of secondary and primary alcohols with phenylsilane
    • Barton, D.H.R., Jang, D.O., & Jaszberenyi, J.Cs. (1991c). Radical deoxygenation of secondary and primary alcohols with phenylsilane. Tetrahedron Letters, 32, 7187-7190.
    • (1991) Tetrahedron Letters , vol.32 , pp. 7187-7190
    • Barton, D.H.R.1    Jang, D.O.2    Jaszberenyi, J.Cs.3
  • 6
    • 0026686954 scopus 로고
    • Hypophosphorous acid and its salts: New reagents for radical chain deoxygenation, dehalogenation and deamination
    • Barton, D.H.R., Jang, D.O., & Jaszberenyi, J.Cs. (1992a). Hypophosphorous acid and its salts: New reagents for radical chain deoxygenation, dehalogenation and deamination. Tetrahedron Letters, 33, 5709-5712.
    • (1992) Tetrahedron Letters , vol.33 , pp. 5709-5712
    • Barton, D.H.R.1    Jang, D.O.2    Jaszberenyi, J.Cs.3
  • 7
    • 0027291622 scopus 로고
    • The invention of radical reactions. Part XXXI. Diphenylsilane: A reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo and iodo compounds by radical chain chemistry
    • Barton, D.H.R., Jang, D.O., & Jaszberenyi, J.Cs. (1993). The invention of radical reactions. Part XXXI. Diphenylsilane: A reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo and iodo compounds by radical chain chemistry. Tetrahedron, 33, 7193-7214.
    • (1993) Tetrahedron , vol.33 , pp. 7193-7214
    • Barton, D.H.R.1    Jang, D.O.2    Jaszberenyi, J.Cs.3
  • 9
    • 0028026210 scopus 로고
    • Pentacyclic triterpene acids in olives
    • Bianchi, G., Pozzi, N., & Vlahov, G. (1994). Pentacyclic triterpene acids in olives. Phytochemistry, 37, 205-207.
    • (1994) Phytochemistry , vol.37 , pp. 205-207
    • Bianchi, G.1    Pozzi, N.2    Vlahov, G.3
  • 10
    • 0000392985 scopus 로고
    • Direct conversion of oxiranes to alkenes by chlorotrimethylsilane and sodium iodide
    • Caputo, R., Mangoni, L., Neri, O., & Palumbo, G. (1981). Direct conversion of oxiranes to alkenes by chlorotrimethylsilane and sodium iodide. Tetrahedron Letters, 22, 3551-3552.
    • (1981) Tetrahedron Letters , vol.22 , pp. 3551-3552
    • Caputo, R.1    Mangoni, L.2    Neri, O.3    Palumbo, G.4
  • 11
    • 33748636029 scopus 로고    scopus 로고
    • Water: The ideal hydrogen-atom source in free-radical chemistry mediated by Ti III and other single-electron-transfer metals?
    • Cuerva, J.M., Campaña, A.G., Justicia, J., Rosales, A., Oller-Lopez, J.L., Robles, R., et al. (2006). Water: The ideal hydrogen-atom source in free-radical chemistry mediated by Ti III and other single-electron-transfer metals? Angewandte Chemie International Edition, 45, 5522-5526.
    • (2006) Angewandte Chemie International Edition , vol.45 , pp. 5522-5526
    • Cuerva, J.M.1    Campaña, A.G.2    Justicia, J.3    Rosales, A.4    Oller-Lopez, J.L.5    Robles, R.6
  • 12
    • 0031882645 scopus 로고    scopus 로고
    • Catalytic, highly regio-and chemoselective generation of radicals from epoxides: Titanocene dichloride as an electron transfer catalyst in transition metal catalyzed radical reactions
    • Gansaüer, A., Pierobon, M., & Bluhm, H. (1998). Catalytic, highly regio-and chemoselective generation of radicals from epoxides: Titanocene dichloride as an electron transfer catalyst in transition metal catalyzed radical reactions. Angewandte Chemie International Edition, 37, 101-103.
    • (1998) Angewandte Chemie International Edition , vol.37 , pp. 101-103
    • Gansaüer, A.1    Pierobon, M.2    Bluhm, H.3
  • 15
    • 0037941123 scopus 로고    scopus 로고
    • Epoxides, cyclic sulfites, and sulfate from natural pentacyclic triterpenoids: Theoretical calculations and chemical transformations
    • Garcia-Granados, A., Lopez, P.E., Melguizo, E., Moliz, J.N., Parra, A., & Simeo, Y. (2003a). Epoxides, cyclic sulfites, and sulfate from natural pentacyclic triterpenoids: Theoretical calculations and chemical transformations. Journal of Organic Chemistry, 68, 4833-4844.
    • (2003) Journal of Organic Chemistry , vol.68 , pp. 4833-4844
    • Garcia-Granados, A.1    Lopez, P.E.2    Melguizo, E.3    Moliz, J.N.4    Parra, A.5    Simeo, Y.6
  • 16
    • 0042671125 scopus 로고    scopus 로고
    • Degradation of triterpenic compounds from olive-pressing residues. Synthesis of trans-decalin type chiral synthons
    • Garcia-Granados, A., Lopez, P.E., Melguizo, E., Parra, A., & Simeo, Y. (2003b). Degradation of triterpenic compounds from olive-pressing residues. Synthesis of trans-decalin type chiral synthons. Tetrahedron Letters, 44, 6673-6677.
    • (2003) Tetrahedron Letters , vol.44 , pp. 6673-6677
    • Garcia-Granados, A.1    Lopez, P.E.2    Melguizo, E.3    Parra, A.4    Simeo, Y.5
  • 17
    • 0742272065 scopus 로고    scopus 로고
    • Partial synthesis of C-ring derivatives from oleanolic and maslinic acids. Formation of several triene systems by chemical and photochemical isomerization processes
    • Garcia-Granados, A., Lopez, P.E., Melguizo, E., Parra, A., & Simeo, Y. (2004a). Partial synthesis of C-ring derivatives from oleanolic and maslinic acids. Formation of several triene systems by chemical and photochemical isomerization processes. Tetrahedron, 60, 1491-1503.
    • (2004) Tetrahedron , vol.60 , pp. 1491-1503
    • Garcia-Granados, A.1    Lopez, P.E.2    Melguizo, E.3    Parra, A.4    Simeo, Y.5
  • 18
    • 19244377601 scopus 로고    scopus 로고
    • Oxidation of several triterpenic diene and triene systems. Oxidative cleavage to obtain chiral intermediates for drimane and phenanthrene semi-synthesis
    • Garcia-Granados, A., Lopez, P.E., Melguizo, E., Parra, A., & Simeo, Y. (2004b). Oxidation of several triterpenic diene and triene systems. Oxidative cleavage to obtain chiral intermediates for drimane and phenanthrene semi-synthesis. Tetrahedron, 60, 3831-3845.
    • (2004) Tetrahedron , vol.60 , pp. 3831-3845
    • Garcia-Granados, A.1    Lopez, P.E.2    Melguizo, E.3    Parra, A.4    Simeo, Y.5
  • 19
    • 33750090341 scopus 로고    scopus 로고
    • Reactivity of chiral sesquiterpene synthons obtained by the degradation of maslinic acid from olive-pressing residues
    • Garcia-Granados, A., Lopez, P.E., Melguizo, E., Parra, A., & Simeo, Y. (2006). Reactivity of chiral sesquiterpene synthons obtained by the degradation of maslinic acid from olive-pressing residues. Synthetic Communications, 36, 3001-3018.
    • (2006) Synthetic Communications , vol.36 , pp. 3001-3018
    • Garcia-Granados, A.1    Lopez, P.E.2    Melguizo, E.3    Parra, A.4    Simeo, Y.5
  • 20
    • 34247557958 scopus 로고    scopus 로고
    • Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A
    • Garcia-Granados, A., Lopez, P.E., Melguizo, E., Parra, A., & Simeo, Y. (2007). Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A. Journal of Organic Chemistry, 72, 3500-3509.
    • (2007) Journal of Organic Chemistry , vol.72 , pp. 3500-3509
    • Garcia-Granados, A.1    Lopez, P.E.2    Melguizo, E.3    Parra, A.4    Simeo, Y.5
  • 23
    • 33845747745 scopus 로고    scopus 로고
    • Process for the industrial recovery of oleanolic and maslinic acids contained in the olive milling subproducts
    • Garcia-Granados, A., Martinez, A., Parra, A., & Rivas, F. (1998c). Process for the industrial recovery of oleanolic and maslinic acids contained in the olive milling subproducts. Chemical Abstracts, International Patent: 128:179706.
    • (1998) Chemical Abstracts International Patent , vol.128 , pp. 179706
    • Garcia-Granados, A.1    Martinez, A.2    Parra, A.3    Rivas, F.4
  • 24
    • 33947441366 scopus 로고
    • Simple modification of the Wolff-Kishner reduction
    • Huang-Minlon, J. (1946). Simple modification of the Wolff-Kishner reduction. Journal of American Chemical Society, 68, 2487-2488.
    • (1946) Journal of American Chemical Society , vol.68 , pp. 2487-2488
    • Huang-Minlon, J.1
  • 25
    • 0000495151 scopus 로고
    • Reduction of steroid ketones and other carbonyl compounds by modified Wolff-Kishner method
    • Huang-Minlon, J. (1949). Reduction of steroid ketones and other carbonyl compounds by modified Wolff-Kishner method. Journal of American Chemical Society, 71, 3301-3303.
    • (1949) Journal of American Chemical Society , vol.71 , pp. 3301-3303
    • Huang-Minlon, J.1
  • 26
    • 0000584803 scopus 로고
    • Reduction of C=X to CH2 by Wolff-Kishner and other hydrazone methods
    • B.M. Trost & I. Fleming (Eds.), Oxford: Pergamon Press
    • Hutchins, R.O., & Hutchins, M.K. (1991). Reduction of C=X to CH2 by Wolff-Kishner and other hydrazone methods. In B.M. Trost & I. Fleming (Eds.), Comprehensive organic synthesis (Vol. 8, pp. 327-343). Oxford: Pergamon Press.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 327-343
    • Hutchins, R.O.1    Hutchins, M.K.2
  • 27
    • 0035808918 scopus 로고    scopus 로고
    • Radical deoxygenation of alcohols via their trifluoroacetate derivatives with diphenylsilane
    • Jang, D.O., Kim, J., Cho, D.H., & Chung, C.M. (2001). Radical deoxygenation of alcohols via their trifluoroacetate derivatives with diphenylsilane. Tetrahedron Letters, 42, 1073-1075.
    • (2001) Tetrahedron Letters , vol.42 , pp. 1073-1075
    • Jang, D.O.1    Kim, J.2    Cho, D.H.3    Chung, C.M.4
  • 28
    • 1642387676 scopus 로고    scopus 로고
    • Radical deoxygenation of tertiary alcohols via trifluoroacetates
    • Kim, J., Cho, D.H., & Jang, D.O. (2004). Radical deoxygenation of tertiary alcohols via trifluoroacetates. Tetrahedron Letters, 45, 3031-3033.
    • (2004) Tetrahedron Letters , vol.45 , pp. 3031-3033
    • Kim, J.1    Cho, D.H.2    Jang, D.O.3
  • 29
    • 0030800209 scopus 로고    scopus 로고
    • Bu3SnH-Catalyzed Barton-McCombie deoxygenation of alcohols
    • Lopez, R.M., Hays, D.S., & Fu, G.C. (1997). Bu3SnH-Catalyzed Barton-McCombie deoxygenation of alcohols. Journal of American Chemical Society, 119, 6949-6950.
    • (1997) Journal of American Chemical Society , vol.119 , pp. 6949-6950
    • Lopez, R.M.1    Hays, D.S.2    Fu, G.C.3
  • 30
    • 33845280764 scopus 로고
    • Transition-metal-centered radicals in organic synthesis. Titanium(III)-induced cyclization of epoxy olefins
    • Nugent, W.A., & Rajanbabu, T.V. (1988). Transition-metal-centered radicals in organic synthesis. Titanium(III)-induced cyclization of epoxy olefins. Journal of American Chemical Society, 110, 8561-8562.
    • (1988) Journal of American Chemical Society , vol.110 , pp. 8561-8562
    • Nugent, W.A.1    Rajanbabu, T.V.2
  • 31
    • 33845184270 scopus 로고
    • Intermolecular addition of epoxides to activated olefins: A new reaction
    • Nugent, W.A., & Rajanbabu, T.V. (1989). Intermolecular addition of epoxides to activated olefins: A new reaction. Journal of American Chemical Society, 111, 4525-4527.
    • (1989) Journal of American Chemical Society , vol.111 , pp. 4525-4527
    • Nugent, W.A.1    Rajanbabu, T.V.2
  • 32
    • 0040155755 scopus 로고
    • Selective generation of free radicals from epoxides using a transition-metal radical. A powerful new tool for organic synthesis
    • Nugent, W.A., & Rajanbabu, T.V. (1994). Selective generation of free radicals from epoxides using a transition-metal radical. A powerful new tool for organic synthesis. Journal of American Chemical Society, 116, 986-997.
    • (1994) Journal of American Chemical Society , vol.116 , pp. 986-997
    • Nugent, W.A.1    Rajanbabu, T.V.2
  • 34
    • 58949086491 scopus 로고    scopus 로고
    • Solution-and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides
    • Parra, A., Rivas, F., Lopez, P.E., Garcia-Granados, A., Martinez, A., Albericio, F., et al. (2009). Solution-and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides. Bioorganic and Medicinal Chemistry, 17, 1139-1145.
    • (2009) Bioorganic and Medicinal Chemistry , vol.17 , pp. 1139-1145
    • Parra, A.1    Rivas, F.2    Lopez, P.E.3    Garcia-Granados, A.4    Martinez, A.5    Albericio, F.6
  • 35
    • 0000872509 scopus 로고
    • Reaction of some trisubstituted steroid epoxides with triphenylphosphine-iodine complex. Deoxygenation of epoxides
    • Paryzek, Z., & Wydra, R. (1984). Reaction of some trisubstituted steroid epoxides with triphenylphosphine-iodine complex. Deoxygenation of epoxides. Tetrahedron Letters, 25, 2601-2604.
    • (1984) Tetrahedron Letters , vol.25 , pp. 2601-2604
    • Paryzek, Z.1    Wydra, R.2


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