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Volumn 68, Issue 23, 2003, Pages 8879-8882

Concise Enantioselective Synthesis of 3,5-Dialkyl-Substituted Indolizidine Alkaloids via Sequential Cross-Metathesis - Double-Reductive Cyclization

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE SYNTHESIS;

EID: 0242660858     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0346095     Document Type: Article
Times cited : (72)

References (72)
  • 51
    • 0035232404 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York
    • (a) Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 2001; Vol. 55, pp 91-258.
    • (2001) The Alkaloids , vol.55 , pp. 91-258
    • Michael, J.P.1
  • 52
    • 77957031616 scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York
    • (b) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44, pp 189-256.
    • (1993) The Alkaloids , vol.44 , pp. 189-256
    • Takahata, H.1    Momose, T.2
  • 59
    • 0029074224 scopus 로고
    • and references cited therein
    • (d) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400 and references cited therein.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5399-5400
    • Munchhof, M.J.1    Meyers, A.I.2
  • 60
    • 0027380329 scopus 로고
    • For a synthesis of (3R,5S,9S)-3-ethyl-5-methylindolizidine (15b), see: Takahata, H.; Bandoh, H.; Momose, T. Tetrahedron 1993, 49, 11205-11212.
    • (1993) Tetrahedron , vol.49 , pp. 11205-11212
    • Takahata, H.1    Bandoh, H.2    Momose, T.3
  • 66
    • 0242452549 scopus 로고    scopus 로고
    • note
    • 19F NMR, GC-MS), see ref 22.
  • 67
    • 0038644039 scopus 로고    scopus 로고
    • To our knowledge, this is the first example of a Ru-catalyzed metathesis reaction of an azide. For RCM of an azide using Schrock's molybdenum catalyst, see: Fürstner, A.; Thiel, O. J. Org. Chem. 2000, 65, 1738-1742.
    • (2000) J. Org. Chem. , vol.65 , pp. 1738-1742
    • Fürstner, A.1    Thiel, O.2
  • 69
    • 0242536271 scopus 로고    scopus 로고
    • note
    • Butyl vinyl ketone 11a was prepared according to Stetter et al., see ref 25.
  • 71
    • 0242705223 scopus 로고    scopus 로고
    • note
    • Slightly lower yields of 14a were obtained by reducing the catalyst loading (3 mol % [Ru-2], 72% yield) or using [Ru-1] (5mol %, 82% yield).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.