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Tetrahedron Letters
Volumn 33, Issue 21, 1992, Pages 2995-2998
An alternative total synthesis of rutaecarpine and vasicolinone alkaloids
Author keywords

[No Author keywords available]
Indexed keywords

ALKALOID; RUTAECARPINE; UNCLASSIFIED DRUG; VASICOLINONE;
EID: 0026683553     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)79581-5     Document Type: Article
Times cited : (33)
References (30)
  • 4
    • 77957043084 scopus 로고
    • and references cited therein.
    • (1983) Alkaloids , vol.21 , pp. 29-54
    • Bergman1
  • 6
    • 0009394701 scopus 로고
    • A Short Synthesis of Rutecarpine and/or Vasicolinone from 2-Chloro-3-(indol-3-yl)ethylquinazolin-4(3H)-one: Evidence for the Participation of the Spiro Intermediate
    • (1985) HETEROCYCLES , vol.23 , pp. 1385-1390
    • Kaneko1    Chiba2    Kasai3    Miwa4
  • 17
    • 77957055412 scopus 로고
    • and references cited therein.
    • (1986) Alkaloids , vol.29 , pp. 99-140
    • Johne1
  • 25
    • 84914351469 scopus 로고    scopus 로고
    • 3, TMS, ppm), δ 45.0 (t, C-1), 24.4 (t, C-2); 46.7 (d, C-3), 149.8 (s, C-3a), 149.2 (s, C-4a), 125.9 (d, C-5), 134.3 (d, C-6 and C-7), 127.3 (d, C-8), 120.6 (s, C-8a), 160.1 (s, C-9), 136.9 (d, C-3′), 119.9, 129.2, 118.2, and 145.8 (carbons of Ph).
  • 26
    • 84914351468 scopus 로고    scopus 로고
    • Semiempirical quantum chemical calculation by AM1 method indicated that the heart of formation of rutaecarpine (6) (322.58 KJ/mol) is about 70KJ/mol less than that of the most stable conformation of spiro compound (5) (391.18 KJ/mol).
  • 30
    • 84914351467 scopus 로고    scopus 로고
    • To solution of hydrazone (4) in DMF saturated ethanolic hydrogen chloride was added at 0°C. The precipitated hydrochloride salt of hydrazone (4) was filtered off. Yield 78 %, m.p.:〉 217°C (decomp).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.