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Volumn 8, Issue 24, 2006, Pages 5665-5668

High-pressure Diels-Alder approach to natural kainic acid

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HYDROXYPROLINE; KAINIC ACID; MARINE TOXIN;

EID: 33845972237     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062419l     Document Type: Article
Times cited : (35)

References (49)
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    • (-)-Kainic acid has also been isolated from Centrocerus clavulatum [(b) Impellizzeri, G.; Mangiafico, G.; Oriente, G.; Piattelli, M.; Sciuto, S.; Fattorusso, E.; Magno, S.; Santacroce, C.; Sica, D. Phytochemistry 1975, 14, 1549-1557]
    • (-)-Kainic acid has also been isolated from Centrocerus clavulatum [(b) Impellizzeri, G.; Mangiafico, G.; Oriente, G.; Piattelli, M.; Sciuto, S.; Fattorusso, E.; Magno, S.; Santacroce, C.; Sica, D. Phytochemistry 1975, 14, 1549-1557]
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    • and from Alsidum helmithocorton [(c) Balansard, G.; Pellegrini, M.; Cavalli, C.; Timon-David, P. Ann. Pharm. Fr. 1983, 41, 77-86].
    • and from Alsidum helmithocorton [(c) Balansard, G.; Pellegrini, M.; Cavalli, C.; Timon-David, P. Ann. Pharm. Fr. 1983, 41, 77-86].
  • 4
    • 33845974205 scopus 로고    scopus 로고
    • Since the beginning of 2006, over 300 papers have been published on the use of kainic acid for the study of various neuronal disorders
    • Since the beginning of 2006, over 300 papers have been published on the use of kainic acid for the study of various neuronal disorders.
  • 5
    • 29944436494 scopus 로고    scopus 로고
    • Shortage of Kainic Acid Hampers Neuroscience Research
    • Shortage of Kainic Acid Hampers Neuroscience Research. Chem. Eng. News 2000, 78 (1), 14-15.
    • (2000) Chem. Eng. News , vol.78 , Issue.1 , pp. 14-15
  • 6
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    • Producers Strive to Bring Kainic Acid Back on the Market
    • Producers Strive to Bring Kainic Acid Back on the Market. Chem. Eng. News 2000, 78 (10), 31.
    • (2000) Chem. Eng. News , vol.78 , Issue.10 , pp. 31
  • 7
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    • For syntheses prior to 2002, see: a
    • For syntheses prior to 2002, see: (a) Parsons, A. F. Tetrahedron 1996, 52, 4149-4174.
    • (1996) Tetrahedron , vol.52 , pp. 4149-4174
    • Parsons, A.F.1
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    • and references cited therein
    • (b) Moloney, M. G. Nat. Prod. Rep. 2002, 19, 597-616 and references cited therein.
    • (2002) Nat. Prod. Rep , vol.19 , pp. 597-616
    • Moloney, M.G.1
  • 9
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    • For more recent syntheses, see: c
    • For more recent syntheses, see: (c) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467-1470.
    • (2003) Org. Lett , vol.5 , pp. 1467-1470
    • Trost, B.M.1    Rudd, M.T.2
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    • Six-membered ring dienophiles: (a) Danishefsky, S.; Kitahara, T.; Yan, C. F.; Morris, J. J. Am. Chem. Soc. 1979, 101, 6996-7000.
    • Six-membered ring dienophiles: (a) Danishefsky, S.; Kitahara, T.; Yan, C. F.; Morris, J. J. Am. Chem. Soc. 1979, 101, 6996-7000.
  • 21
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    • Acyclic dienophiles: (f) Paczkowski, R.; Maichle-Mossmer, C.; Maier, M. E. Org. Lett. 2000, 2, 3967-3969.
    • Acyclic dienophiles: (f) Paczkowski, R.; Maichle-Mossmer, C.; Maier, M. E. Org. Lett. 2000, 2, 3967-3969.
  • 22
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    • Five-membered carbocycles with cyclopentadiene: (a) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561-1562.
    • Five-membered carbocycles with cyclopentadiene: (a) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561-1562.
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    • With Rawal's diene: (f) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 7843-7844.
    • With Rawal's diene: (f) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 7843-7844.
  • 28
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    • Furanoside-type dienophiles: (g) Rehnberg, N.; Sundin, A.; Magnusson, G. J. Org. Chem. 1990, 55, 5477-5483.
    • Furanoside-type dienophiles: (g) Rehnberg, N.; Sundin, A.; Magnusson, G. J. Org. Chem. 1990, 55, 5477-5483.
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    • Indole dienophiles: (i) Chataigner, I.; Hess, E.; Toupet, L.; Piettre, S. R. Org. Lett. 2001, 3, 515-518.
    • Indole dienophiles: (i) Chataigner, I.; Hess, E.; Toupet, L.; Piettre, S. R. Org. Lett. 2001, 3, 515-518.
  • 40
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    • Surprisingly, no aldehyde was obtained on treatment of triflate 4 with Pd(0) and tributyltin hydride in DMF under carbon monoxide (only the reduced product 5 was formed). Other approaches to the conjugated aldehyde were low yielding and/or too long.
    • Surprisingly, no aldehyde was obtained on treatment of triflate 4 with Pd(0) and tributyltin hydride in DMF under carbon monoxide (only the reduced product 5 was formed). Other approaches to the conjugated aldehyde were low yielding and/or too long.
  • 42
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    • For a review, see:, van Eldik, R, Klärner, F-G, Eds, Wiley: Weinheim
    • For a review, see: High Pressure Chemistry, van Eldik, R., Klärner, F-G., Eds.; Wiley: Weinheim, 2002.
    • (2002) High Pressure Chemistry
  • 47
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    • For an alternative preparation of this aldehyde (for the synthesis of, )-domoic acid, see ref 6
    • For an alternative preparation of this aldehyde (for the synthesis of (-)-domoic acid), see ref 6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.