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Volumn 130, Issue 41, 2008, Pages 13778-13789

The lyconadins: Enantioselective total syntheses of (+)-lyconadin A and (-)-lyconadin B

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EID: 53849087169     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804939r     Document Type: Article
Times cited : (40)

References (74)
  • 4
    • 25144494663 scopus 로고    scopus 로고
    • For recent reviews of Lycopodium alkaloids, see: a, Cordell, G. A, Ed, Elsevier Academic Press: New York
    • For recent reviews of Lycopodium alkaloids, see: (a) Kobayashi, J.; Morita, H. The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Elsevier Academic Press: New York, 2005; Vol. 61, p 1.
    • (2005) The Alkaloids: Chemistry and Biology , vol.61 , pp. 1
    • Kobayashi, J.1    Morita, H.2
  • 7
    • 77957098031 scopus 로고
    • Cordell, G. A, Brossi, A, Ed, Academic Press: New York
    • (d) Ayer, W. A.; Trifonov, L. S. Alkaloids; Cordell, G. A., Brossi, A., Ed.; Academic Press: New York, 1994; Vol. 45, p 233.
    • (1994) Alkaloids , vol.45 , pp. 233
    • Ayer, W.A.1    Trifonov, L.S.2
  • 9
    • 77957072064 scopus 로고
    • Brossi, A, Ed, Academic Press: New York
    • (f) MacLean, D. B. The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 241.
    • (1985) The Alkaloids , vol.26 , pp. 241
    • MacLean, D.B.1
  • 10
    • 53849085994 scopus 로고    scopus 로고
    • Tracey, M. R.; Hsung, R. Abstract of Papers, Presented at the 226th National Meeting of the American Chemical Society, New York, September 2003; paper ORGN-721.
    • (a) Tracey, M. R.; Hsung, R. Abstract of Papers, Presented at the 226th National Meeting of the American Chemical Society, New York, September 2003; paper ORGN-721.
  • 16
  • 20
    • 0001512268 scopus 로고    scopus 로고
    • While 7-endo-trig conjugate additions are known, their application to the formation of a [5.4.0]undecane-2,7-dione is only precedented from Tokoroyama's studies toward the clerodane diterpenoids: Tokoroyama, T.; Tsukamoto, M.; Iio, H. Tetrahedron Lett. 1984, 25, 5067.
    • While 7-endo-trig conjugate additions are known, their application to the formation of a [5.4.0]undecane-2,7-dione is only precedented from Tokoroyama's studies toward the clerodane diterpenoids: Tokoroyama, T.; Tsukamoto, M.; Iio, H. Tetrahedron Lett. 1984, 25, 5067.
  • 27
    • 34247133512 scopus 로고    scopus 로고
    • New Derivatives of Beta-Amino Acids with Anti-Thrombotic Activity
    • Eur. Patent EP 0 560 730 B1, 1996
    • Kottirsch, G.; Metternich, R.; New Derivatives of Beta-Amino Acids with Anti-Thrombotic Activity. Eur. Patent EP 0 560 730 B1, 1996.
    • Kottirsch, G.1    Metternich, R.2
  • 30
    • 0024456198 scopus 로고    scopus 로고
    • 4: (a) Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673.
    • 4: (a) Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673.
  • 32
    • 0001173496 scopus 로고    scopus 로고
    • 4: (c) Umino, N.; Iwakuma, T.; Itoh, N. Tetrahedron Lett. 1976, 10, 763.
    • 4: (c) Umino, N.; Iwakuma, T.; Itoh, N. Tetrahedron Lett. 1976, 10, 763.
  • 34
    • 0028871677 scopus 로고    scopus 로고
    • Red-A1: (e) Fréville, S.; Célérier, J. P.; Thuy, V. M.; Lhommet, G. Tetrahedron: Asymmetry 1995, 6, 2651.
    • Red-A1: (e) Fréville, S.; Célérier, J. P.; Thuy, V. M.; Lhommet, G. Tetrahedron: Asymmetry 1995, 6, 2651.
  • 35
    • 0030828305 scopus 로고    scopus 로고
    • 3: (f) Batistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Fava, G. G.; Ferrari, M. B.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975.
    • 3: (f) Batistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Fava, G. G.; Ferrari, M. B.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975.
  • 36
    • 53849101671 scopus 로고    scopus 로고
    • Masking the hydroxyl as the TBS ether did not improve amide reduction
    • Masking the hydroxyl as the TBS ether did not improve amide reduction.
  • 37
    • 0017892114 scopus 로고    scopus 로고
    • Thioamide formation was accomplished utilizing Lawesson's Reagent: Pedersen, B. S.; Scheibye, S.; Nilsson, N. H.; Lawesson, S. O. Bull. Soc. Chim. Belg. 1978, 87, 223.
    • Thioamide formation was accomplished utilizing Lawesson's Reagent: Pedersen, B. S.; Scheibye, S.; Nilsson, N. H.; Lawesson, S. O. Bull. Soc. Chim. Belg. 1978, 87, 223.
  • 38
    • 53849146192 scopus 로고    scopus 로고
    • See Supporting Information for preparation of, -26
    • See Supporting Information for preparation of (-)-26.
  • 45
    • 53849115932 scopus 로고    scopus 로고
    • Gaussian, Inc, Wallingford, CT, See Supporting Information for details regarding the described calculations
    • Frisch, M. J. Gaussian 03, revision C.01; Gaussian, Inc.: Wallingford, CT, 2004. See Supporting Information for details regarding the described calculations.
    • (2004) Gaussian 03, revision , Issue.C.01
    • Frisch, M.J.1
  • 46
    • 53849126335 scopus 로고    scopus 로고
    • Single crystal X-ray crystallographic analysis unambiguously confirmed the structural identity of compound, -42. See Supporting Information for details
    • Single crystal X-ray crystallographic analysis unambiguously confirmed the structural identity of compound (-)-42. See Supporting Information for details.
  • 47
    • 0001529798 scopus 로고    scopus 로고
    • 13C-NMR shifts have been observed for hemiaminal salts; see: Hext, N. M.; Hansen, J.; Blake, A. J.; Hibbs, D. E.; Hursthouse, M. B.; Shishkin, O. V.; Mascal, M. J. Org. Chem. 1998, 63, 6016.
    • 13C-NMR shifts have been observed for hemiaminal salts; see: Hext, N. M.; Hansen, J.; Blake, A. J.; Hibbs, D. E.; Hursthouse, M. B.; Shishkin, O. V.; Mascal, M. J. Org. Chem. 1998, 63, 6016.
  • 48
    • 53849139611 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 51
    • 53849126334 scopus 로고    scopus 로고
    • Increasing reaction time for the epimerization of (-)-42 to 46 did not effect the ratio after 18 h (1:3, respectively), suggesting that this represents the equilibrium mixture for the specified conditions.
    • Increasing reaction time for the epimerization of (-)-42 to 46 did not effect the ratio after 18 h (1:3, respectively), suggesting that this represents the equilibrium mixture for the specified conditions.
  • 52
    • 53849105965 scopus 로고    scopus 로고
    • 2) afforded a mixture of silylated secondary hydroxyl, the epimeric C(12) protected silylated secondary hydroxyl, as well as the bissilylated secondary hydroxyl C(5) and C(12) enol ether. These reaction byproducts were minimized by employing 2,6-di-tert-butyl-4-methylpyridine (DtBMP) as a base.
    • 2) afforded a mixture of silylated secondary hydroxyl, the epimeric C(12) protected silylated secondary hydroxyl, as well as the bissilylated secondary hydroxyl C(5) and C(12) enol ether. These reaction byproducts were minimized by employing 2,6-di-tert-butyl-4-methylpyridine (DtBMP) as a base.
  • 64
    • 53849109363 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 66
    • 38749083069 scopus 로고    scopus 로고
    • Formation of compound (-)-61 can be understood as a conjugate addition of cyanide to the unsaturated amide prior to ring closure, followed by ring closure, and then oxidation, thermodynamically driven by aromatization to the α-pyridinone ring. See the following reference for a similar eliminative, aromatization event: Donohue, T. J.; Fishlock, L. P.; Procopiou, P. A. Org. Lett. 2008, 10, 285.
    • Formation of compound (-)-61 can be understood as a conjugate addition of cyanide to the unsaturated amide prior to ring closure, followed by ring closure, and then oxidation, thermodynamically driven by aromatization to the α-pyridinone ring. See the following reference for a similar eliminative, aromatization event: Donohue, T. J.; Fishlock, L. P.; Procopiou, P. A. Org. Lett. 2008, 10, 285.
  • 68
    • 10644266761 scopus 로고    scopus 로고
    • Conditions examined to convert 63 or 64 to (-)-lyconadin B (2) included: Resubjection to reaction conditions. Treatment with acid: (a) Kan, W. M.; Cheng, C.-L.; Chern, C.-Y Synth. Commun. 2004, 34, 4257.
    • Conditions examined to convert 63 or 64 to (-)-lyconadin B (2) included: Resubjection to reaction conditions. Treatment with acid: (a) Kan, W. M.; Cheng, C.-L.; Chern, C.-Y Synth. Commun. 2004, 34, 4257.
  • 69
    • 0040595025 scopus 로고    scopus 로고
    • Thermal dehydration: (b) Citterio, A.; Carnevali, E.; Farina, A.; Meille, V.; Alini, S.; Cotarca, L. Org. Prep. Proced. Int. 1997, 29, 465.
    • Thermal dehydration: (b) Citterio, A.; Carnevali, E.; Farina, A.; Meille, V.; Alini, S.; Cotarca, L. Org. Prep. Proced. Int. 1997, 29, 465.
  • 70
    • 33646858600 scopus 로고    scopus 로고
    • Chemical dehydration: (c) Pawlowski, M.; Maurin, J. K.; Leniewshki, A.; Wojtasiewicz, K.; Czarnocki, Z. Heterocycles 2005, 65, 9.
    • Chemical dehydration: (c) Pawlowski, M.; Maurin, J. K.; Leniewshki, A.; Wojtasiewicz, K.; Czarnocki, Z. Heterocycles 2005, 65, 9.
  • 71
    • 53849087677 scopus 로고    scopus 로고
    • A rationale for differences in the conditions required for optimal formation of (+)-lyconadin A (1) and (-)-lyconadin B (2) is not apparent to the authors.
    • A rationale for differences in the conditions required for optimal formation of (+)-lyconadin A (1) and (-)-lyconadin B (2) is not apparent to the authors.
  • 72
    • 53849125617 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 73
    • 33947088667 scopus 로고    scopus 로고
    • Martin sulfurane was handled and stored according to the procedures described herein: Arhart, R. J.; Martin, J. C. J. Am. Chem. Soc. 1972, 94, 5003.
    • Martin sulfurane was handled and stored according to the procedures described herein: Arhart, R. J.; Martin, J. C. J. Am. Chem. Soc. 1972, 94, 5003.
  • 74
    • 53849125204 scopus 로고    scopus 로고
    • Lithium di-iso-propylamide was prepared as follows: Freshly distilled di-iso-propylamine (1.4 mL, 10 mmol, 1.1 equiv) was dissolved in tetrahydrofuran (15 mL) and cooled to 0°C. n-Butyl lithium (6.6 mL, 1.37 M solution in tetrahydrofuran) was added dropwise over 5 min, and the mixture was stirred for 1 h at 0°C. The resulting lithium di-iso-propylamide solution (0.39 M) was then used immediately in the reaction.
    • Lithium di-iso-propylamide was prepared as follows: Freshly distilled di-iso-propylamine (1.4 mL, 10 mmol, 1.1 equiv) was dissolved in tetrahydrofuran (15 mL) and cooled to 0°C. n-Butyl lithium (6.6 mL, 1.37 M solution in tetrahydrofuran) was added dropwise over 5 min, and the mixture was stirred for 1 h at 0°C. The resulting lithium di-iso-propylamide solution (0.39 M) was then used immediately in the reaction.


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