메뉴 건너뛰기




Volumn , Issue 3, 2005, Pages 610-617

Addition of indole to methyl 2-chloro-2-cyclopropylideneacetate en route to spirocyclopropanated analogues of demethoxyfumitremorgine C and tadalafil

Author keywords

Building blocks; Heterocycles; Natural products; Peptidomimetics; Small ring systems

Indexed keywords

CYCLOPROPANE; DEMETHOXYFUMITREMORGINE C; INDOLE DERIVATIVE; LEWIS ACID; NATURAL PRODUCT; SPIRO COMPOUND; SPIROCYCLOPROPANE; TADALAFIL; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 14344256966     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400617     Document Type: Article
Times cited : (33)

References (50)
  • 19
  • 21
    • 14344265771 scopus 로고    scopus 로고
    • note
    • 3), cf. ref.[7c]
  • 29
    • 14344255258 scopus 로고    scopus 로고
    • A61 K31/4985, 2003; Lilly Icos LLC. Pr.: WO2000US11129, 2000
    • W. E. Pullman, S. J. Whitaker, A61 K31/4985, 2003; Lilly Icos LLC. Pr.: WO2000US11129, 2000.
    • Pullman, W.E.1    Whitaker, S.J.2
  • 37
    • 33748939157 scopus 로고
    • This so-called Thorpe-Ingold effect had originally been attributed to an angle enlargement, see: [14a] R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. 1915, 107, 1080-1106.
    • (1915) J. Chem. Soc. , vol.107 , pp. 1080-1106
    • Beesley, R.M.1    Ingold, C.K.2    Thorpe, J.F.3
  • 39
    • 0001392294 scopus 로고    scopus 로고
    • It was later shown that the major influence stems from the conformational preference of such a system, see: [14c] M. E. Jung, M. Kiankarimi, J. Org. Chem. 1998, 63, 2968-2974.
    • (1998) J. Org. Chem. , vol.63 , pp. 2968-2974
    • Jung, M.E.1    Kiankarimi, M.2
  • 41
    • 0032548137 scopus 로고    scopus 로고
    • The corresponding 2-amino-2-[1-(1H-indol-3-yl)cylopropyl]-acetic acid has already been described, see: D. C. Horwell, M. J. McKiernan, S. Osborne, Tetrahedron Lett. 1998, 39, 8729-8732.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8729-8732
    • Horwell, D.C.1    McKiernan, M.J.2    Osborne, S.3
  • 42
    • 0027481830 scopus 로고
    • Problems with the cyclization of prenaldimines have also been observed by others, see: D. M. Harrison, R. B. Sharma, Tetrahedron 1993, 49, 3165-3184.
    • (1993) Tetrahedron , vol.49 , pp. 3165-3184
    • Harrison, D.M.1    Sharma, R.B.2
  • 47
    • 14344257801 scopus 로고    scopus 로고
    • note
    • On the basis of the known absolute configuration of the employed (S)-proline and the assumption that it did not racemize during incorporation, this depicts the overall absolute configuration as well.
  • 50
    • 14344254105 scopus 로고    scopus 로고
    • note
    • 2 (310.4): calcd. C 73.52, H 7.14, N 9.03; found C 73.19, H 7.15, N 8.91.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.