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Volumn 2, Issue 20, 2000, Pages 3181-3183

A concise route to (-)-kainic acid

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID RECEPTOR BLOCKING AGENT; ANTHELMINTIC AGENT; KAINIC ACID;

EID: 0034609677     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006377r     Document Type: Article
Times cited : (66)

References (27)
  • 3
    • 85037496630 scopus 로고    scopus 로고
    • Pertinent reviews for the synthesis of the kainoid amino acids, see: (a) Reference 2
    • Pertinent reviews for the synthesis of the kainoid amino acids, see: (a) Reference 2.
  • 5
    • 0033180461 scopus 로고    scopus 로고
    • and previous reports
    • (c) Molony, M. G. Nat. Prod. Rep. 1999, 16, 485 and previous reports.
    • (1999) G. Nat. Prod. Rep. , vol.16 , pp. 485
    • Molony, M.1
  • 6
    • 0029767411 scopus 로고    scopus 로고
    • Enantiocontrolled synthesis of (-)-kainic acid reported after ref 3, see: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem 1996, 61, 5418.
    • (1996) J. Org. Chem , vol.61 , pp. 5418
    • Hanessian, S.1    Ninkovic, S.2
  • 13
    • 0033532090 scopus 로고    scopus 로고
    • (g) Cossy, J.; Cases, M.; Pardo, D. G. Synlett 1998, 507 and Tetrahedron 1999, 55, 6153.
    • (1999) Tetrahedron , vol.55 , pp. 6153
  • 17
    • 0028019133 scopus 로고
    • Pertinent review for the hetero-Diels-Alder reaction involving a nitroso dienophile, see: (a) Streith, J.; Defoin, A. Synthesis 1994, 1107.
    • (1994) Synthesis , vol.1107
    • Streith, J.1    Defoin, A.2
  • 19
    • 85037500501 scopus 로고    scopus 로고
    • note
    • Optical purity of the products was determined by HPLC using a column with a chiral stationary phase (CHIRALCEL OD, elution with i-PrOH/hexane 20:80 v/v for 4 and i-PrOH/hexane 10:90 v/v for 2).
  • 20
    • 85037505880 scopus 로고    scopus 로고
    • note
    • Typical Procedure for the Lipase-Mediated Transesterification. A suspension of (±)-2 (503 mg, 2.16 mmol), vinyl acetate (0.2 mL, 2.16 mmol), and Lipase AK (100 mg) in dichloromethane (10 mL) was stirred at room temperature for 48 h. After filtration through a Celite pad, the filtrate was evaporated under reduced pressure and chromatographed (silica gel, elution with AcOEt/hexane, 1:4 to 1:1 v/v) to give (-)-4 (293 mg, 49%) and (-)-2 (225 mg, 45%).
  • 24
    • 0028806603 scopus 로고
    • Addition of sodium hydrogen carbonate was found to suppress decomposition of the substrate, cf. Kamikubo, T.; Ogasawara, K. Chem. Commun. 1995, 1951.
    • (1995) Chem. Commun. , vol.1951
    • Kamikubo, T.1    Ogasawara, K.2
  • 25
    • 85037511955 scopus 로고    scopus 로고
    • note
    • 4 357.1939, found 357.1920.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.