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Volumn 50, Issue 1, 1999, Pages 31-34

A synthesis of (±)-ipalbidine using sulfur-controlled 6-exo selective radical cyclization of α-phenylthio amide

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; INDOLIZIDINE ALKALOID; IPALBIDINE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032864415     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-98-S(H)13     Document Type: Article
Times cited : (20)

References (18)
  • 2
    • 0030913559 scopus 로고    scopus 로고
    • For reviews on the indolizidine alkaloids, and references cited therein
    • For reviews on the indolizidine alkaloids, see: J.P. Michael, Nat. Prod. Rep., 1997, 14, 21 and references cited therein.
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 21
    • Michael, J.P.1
  • 11
  • 12
    • 0345407277 scopus 로고    scopus 로고
    • note
    • 3, 270 MHz) 1.38-2.35 (10 H, m), 3.35-3.45 (1 H, m), 3.55-3.75 (2 H, m), 3.79 (3 H, s, OMe), 3.85-3.98 (1 H, m), 6.85 (2 H, d, J = 8.6 Hz, ArH), 7.13 (2 H, d, J = 8.6 Hz, ArH)].
  • 14
    • 33748646785 scopus 로고    scopus 로고
    • and references cited therein
    • H. Ishibashi, C. Kameoka, H. Iriyama, K. Kodama, T. Sato, and M. Ikeda, J. Org. Chem., 1995, 60, 1276. See also: H. Ishibashi, H. Kawanami, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1997, 817 and references cited therein.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 817
    • Ishibashi, H.1    Kawanami, H.2    Ikeda, M.3
  • 15
    • 0344544971 scopus 로고    scopus 로고
    • note
    • 3, 270 MHz) spectrum of 13 exhibited the signals due to =CH(SPh) at δ 6.19 (d, J = 14.8 Hz) and 6.28 (d, J = 9.2 Hz) for the (E)-and (Z)-isomers, respectively.
  • 16
    • 0344113327 scopus 로고    scopus 로고
    • note
    • 6, 270 MHz) spectrum of 16 exhibited the signals due to 6-H for two stereoisomers at δ 3.56 (d, J = 4.3 Hz) and 3.84 (d, J = 5.6 Hz), respectively.
  • 17
    • 0344113326 scopus 로고    scopus 로고
    • The reason why the α-phenylthio group of 8 did not work as a leaving group is not clear at the moment
    • The reason why the α-phenylthio group of 8 did not work as a leaving group is not clear at the moment.
  • 18
    • 0344113324 scopus 로고    scopus 로고
    • It has been reported that (+)-ipalbidine forms hexagonal crystals from benzene/cyclohexane, but the specfic rotation of this material is not reproducible and depends upon the drying conditions because the crystals contain some benzene and cyclohexane. See ref. 3b
    • It has been reported that (+)-ipalbidine forms hexagonal crystals from benzene/cyclohexane, but the specfic rotation of this material is not reproducible and depends upon the drying conditions because the crystals contain some benzene and cyclohexane. See ref. 3b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.