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Volumn , Issue 2, 2007, Pages 325-334

Synthesis of alkaloid analogues from β-amino alcohols by β-fragmentation of primary alkoxyl radicals

Author keywords

Alkaloids; Amino alcohols; Cleavage reactions; Nitrogen heterocycles; Radical reactions

Indexed keywords


EID: 33846471806     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600720     Document Type: Article
Times cited : (26)

References (133)
  • 4
    • 0000124573 scopus 로고    scopus 로고
    • Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
    • d) W. Zhang in Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, vol. 2, pp. 234-245;
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 234-245
    • Zhang, W.1
  • 5
    • 0000213430 scopus 로고    scopus 로고
    • Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
    • e) E. Suárez, M. S. Rodríguez in Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, vol. 2, pp. 440-454;
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 440-454
    • Suárez, E.1    Rodríguez, M.S.2
  • 8
    • 0034246704 scopus 로고    scopus 로고
    • h) L. Yet, Chem. Rev. 2000, 100, 2963-3007;
    • (2000) Chem. Rev , vol.100 , pp. 2963-3007
    • Yet, L.1
  • 11
    • 0001226680 scopus 로고
    • Ed, R. A. Abramovitch, Plenum Press, New York
    • k) P. Brun, B. Waegell in Reactive Intermediates (Ed.: R. A. Abramovitch), Plenum Press, New York, 1983, vol. 3, pp. 367-426;
    • (1983) Reactive Intermediates , vol.3 , pp. 367-426
    • Brun, P.1    Waegell, B.2
  • 12
    • 0033607760 scopus 로고    scopus 로고
    • See also:, and references cited therein
    • l) See also: S. Wilsey, P. Dowd, K. N. Houk, J. Org. Chem. 1999, 64, 8801-8811 and references cited therein.
    • (1999) J. Org. Chem , vol.64 , pp. 8801-8811
    • Wilsey, S.1    Dowd, P.2    Houk, K.N.3
  • 33
    • 0038208388 scopus 로고    scopus 로고
    • For other interesting examples, see:, and references cited therein
    • u) For other interesting examples, see: A. Boto, D. Hernández, R. Hernández, E. Suárez, J. Org. Chem. 2003, 68, 5310-5319 and references cited therein.
    • (2003) J. Org. Chem , vol.68 , pp. 5310-5319
    • Boto, A.1    Hernández, D.2    Hernández, R.3    Suárez, E.4
  • 40
  • 43
    • 0029036335 scopus 로고
    • and references cited therein
    • d) G. Majetich, K. Wheless, Tetrahedron 1995, 51, 7095-7129 and references cited therein.
    • (1995) Tetrahedron , vol.51 , pp. 7095-7129
    • Majetich, G.1    Wheless, K.2
  • 46
    • 0038317136 scopus 로고    scopus 로고
    • Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim
    • c) J. Hartung in Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, vol. 2, pp. 427-439.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 427-439
    • Hartung, J.1
  • 47
    • 33846533863 scopus 로고    scopus 로고
    • We have recently reported (ref.[2t, that the primary alkoxy radicals derived from carbohydrates in the furanose form gave a mixture of fragmentation and intramolecular hydrogen abstraction IHA, By controlling the reaction conditions, the stereochemistry of the substituents and the protecting groups, the β-fragmentation was made to predominate over the side reactions. In contrast, the substrates described in this article gave scission as the sole reaction
    • [2t]) that the primary alkoxy radicals derived from carbohydrates in the furanose form gave a mixture of fragmentation and intramolecular hydrogen abstraction (IHA). By controlling the reaction conditions, the stereochemistry of the substituents and the protecting groups, the β-fragmentation was made to predominate over the side reactions. In contrast, the substrates described in this article gave scission as the sole reaction.
  • 52
    • 0037064474 scopus 로고    scopus 로고
    • A. Boto, R. Hernández, A. Montoya, E. Suárez, Tetrahedron Lett. 2002, 43, 8269-8272;
    • d) A. Boto, R. Hernández, A. Montoya, E. Suárez, Tetrahedron Lett. 2002, 43, 8269-8272;
  • 59
    • 0141925985 scopus 로고    scopus 로고
    • F. X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693-3712 and references cited therein;
    • a) F. X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693-3712 and references cited therein;
  • 62
    • 0003780442 scopus 로고
    • Eds, P. G. Sammes, J. B. Taylor, Pergamon Press, Oxford, vols, and 3
    • d) Comprehensive Medicinal Chemistry (Eds.: P. G. Sammes, J. B. Taylor), Pergamon Press, Oxford, 1990, vols. 2 and 3.
    • (1990) Comprehensive Medicinal Chemistry , vol.2
  • 78
    • 26844582966 scopus 로고    scopus 로고
    • For serial reviews on indolizidine and quinolizidine alkaloids, see: J. P. Michael, Nat. Prod. Rep. 2005, 22, 603-626 and references cited therein;
    • a) For serial reviews on indolizidine and quinolizidine alkaloids, see: J. P. Michael, Nat. Prod. Rep. 2005, 22, 603-626 and references cited therein;
  • 80
    • 0000584109 scopus 로고    scopus 로고
    • Alkaloid Glycosidase Inhibitors
    • Eds, D. H. R. Barton, K. Nakanishi, O. Meth-Cohn, Elsevier, Oxford, ch. 7;
    • c) A. D. Elbein, R. J. Molyneux, "Alkaloid Glycosidase Inhibitors" in Comprehensive Natural Products Chemistry (Eds.: D. H. R. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Oxford, 1999, vol. 3, ch. 7;
    • (1999) Comprehensive Natural Products Chemistry , vol.3
    • Elbein, A.D.1    Molyneux, R.J.2
  • 83
    • 1442360753 scopus 로고    scopus 로고
    • R. H. Grubbs Ed, Wiley-VCH, Weinheim
    • R. H. Grubbs (Ed.), Handbook of Metathesis, Wiley-VCH, Weinheim, 2003.
    • (2003) Handbook of Metathesis
  • 84
    • 0036910440 scopus 로고    scopus 로고
    • For serial reviews on pyrrolizidine alkaloids, see: J. R. Lidell, Nat. Prod. Rep. 2002, 19, 773-781 and references cited therein;
    • a) For serial reviews on pyrrolizidine alkaloids, see: J. R. Lidell, Nat. Prod. Rep. 2002, 19, 773-781 and references cited therein;
  • 85
    • 0004052642 scopus 로고
    • For other reviews and books, see: A. F. M. Rizk Ed, CRC Press, Boston
    • b) For other reviews and books, see: A. F. M. Rizk (Ed.), Naturally Occurring Pyrrolizidine Alkaloids, CRC Press, Boston, 1991;
    • (1991) Naturally Occurring Pyrrolizidine Alkaloids
  • 89
    • 0037450388 scopus 로고    scopus 로고
    • and references cited therein
    • f) H. Yoda, T. Egawa, K. Takabe, Tetrahedron Lett. 2003, 44, 1643-1646 and references cited therein.
    • (2003) Tetrahedron Lett , vol.44 , pp. 1643-1646
    • Yoda, H.1    Egawa, T.2    Takabe, K.3
  • 91
    • 0009929120 scopus 로고    scopus 로고
    • Plant Chemical Ecology
    • Eds, D. H. R. Barton, K. Nakanishi, O. Meth-Cohn, Elsevier, Oxford, ch. 3;
    • b) J. B. Harborne, "Plant Chemical Ecology" in Comprehensive Natural Products Chemistry (Eds.: D. H. R. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Oxford, 1999, vol. 8, ch. 3;
    • (1999) Comprehensive Natural Products Chemistry , vol.8
    • Harborne, J.B.1
  • 92
    • 33846548792 scopus 로고    scopus 로고
    • E. D. Morgan, I. D. Wilson, Insect Hormones and Insect Chemical Ecology in Comprehensive Natural Products Chemistry (Eds.: D. H., R. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Oxford, 1999, 8, ch. 3;
    • c) E. D. Morgan, I. D. Wilson, "Insect Hormones and Insect Chemical Ecology" in Comprehensive Natural Products Chemistry (Eds.: D. H., R. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Oxford, 1999, vol. 8, ch. 3;
  • 94
    • 33646547234 scopus 로고    scopus 로고
    • Alexines: a I. Izquierdo, M. T. Plaza, J. A. Tamayo, M. Rodríguez, A. Martos, Tetrahedron 2006, 62, 6006-6011;
    • Alexines: a) I. Izquierdo, M. T. Plaza, J. A. Tamayo, M. Rodríguez, A. Martos, Tetrahedron 2006, 62, 6006-6011;
  • 101
    • 33846538187 scopus 로고    scopus 로고
    • 1′,2 = 8.8 Hz). For the major diastereomer
    • 1′,2 2 = 9.3 Hz;
    • , vol.1 , Issue.2 , pp. 2
    • Minor diastereomer1
  • 104
    • 0003086615 scopus 로고    scopus 로고
    • erythro, see: J.-L. Bougeois, L. Stella, J.-M. Surzur, Tetrahedron Lett. 1981, 22, 61-64.
    • erythro, see: J.-L. Bougeois, L. Stella, J.-M. Surzur, Tetrahedron Lett. 1981, 22, 61-64.
  • 105
    • 33846478083 scopus 로고    scopus 로고
    • Since both the old and the new batches were purchased from the same company, the different reaction results suggested that the old reagent isomerized prior to use. The isomerization of disubstituted olefins to trisubstituted alkenes is favored on thermodynamic grounds, and small amounts of acid can catalyze the process. Since chlorinated reagents release HCl with time, the isomerization could easily take place. See also: Shell Devel. Co. Patent US2042223 (1934);
    • a) Since both the old and the new batches were purchased from the same company, the different reaction results suggested that the old reagent isomerized prior to use. The isomerization of disubstituted olefins to trisubstituted alkenes is favored on thermodynamic grounds, and small amounts of acid can catalyze the process. Since chlorinated reagents release HCl with time, the isomerization could easily take place. See also: Shell Devel. Co. Patent US2042223 (1934);
  • 106
    • 33846544002 scopus 로고
    • For related isomerizations, see: Patent US 2097154
    • b) For related isomerizations, see: Shell Devel. Co. Patent US 2097154 (1933);
    • (1933)
    • Shell Devel, C.1
  • 108
    • 0024584348 scopus 로고    scopus 로고
    • Sedamine analogues: P.-J. Tirel, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 1947-1950;
    • a) Sedamine analogues: P.-J. Tirel, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 1947-1950;
  • 117
    • 0035897085 scopus 로고    scopus 로고
    • For reviews on the subject, see
    • e) For reviews on the subject, see: S. K. Bur, S. F. Martin, Tetrahedron 2001, 57, 3221-3242;
    • (2001) Tetrahedron , vol.57 , pp. 3221-3242
    • Bur, S.K.1    Martin, S.F.2
  • 122
    • 0034614462 scopus 로고    scopus 로고
    • For related examples, see
    • c) For related examples, see: M. Lombardo, C. Trombini, Tetrahedron 2000, 56, 323-326;
    • (2000) Tetrahedron , vol.56 , pp. 323-326
    • Lombardo, M.1    Trombini, C.2
  • 125
    • 0001028588 scopus 로고
    • For a related strategy, see
    • For a related strategy, see: N. Ikota, Heterocycles 1993, 36, 2035-2050.
    • (1993) Heterocycles , vol.36 , pp. 2035-2050
    • Ikota, N.1
  • 131
    • 33846498149 scopus 로고    scopus 로고
    • The assigned stereochemistries were supported by NOESY experiments. Compound 40: Spatial correlations were observed for 2-H (δH 4.10)/Meb (δH 1.46, and for 3-H (δH 4.45)/Mea (δH 1.30)/4-H (δH 4.66, Compound 41: Spatial correlations were observed for: 3-H (δH 4.36)/4a-H (δH 3.51) and 4-Ha (δH 1.40, 5-H (δH 4.24, Compound 42: Spatial correlations were observed for: CH2TMS (δH 1-21 and 0.88)/4a-H (δH 3.58, for 4a-H (δH 3.58)/Meb (δH 1.55, and for 6-H (δH 4.75)/Mea δH 1.36, δH in ppm
    • H in ppm].
  • 132
    • 33846490978 scopus 로고    scopus 로고
    • The assigned stereochemistry for compound 43 was also supported by NOESY experiments. Spatial correlations were observed for 2-H (δH 4.43) and Meb (δH 1-45, for CHaHbCOPh (δH 3.18)/3-H (δH 4.70, for 3-H (δH 4.70)/Mea (δH 1.30)/4-H (δH 4.82, and for 4-H (δH 4.82)/CHaHbCOPh δH 3.44, δH in ppm
    • H in ppm].


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