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Volumn 38, Issue 19, 1999, Pages 2934-2936

Total synthesis of (±)-gelsemine

Author keywords

Alkaloids; Palladium; Pericyclic reactions; Rearrangements; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE; GELSEMINE; UNCLASSIFIED DRUG;

EID: 0033523667     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991004)38:19<2934::AID-ANIE2934>3.0.CO;2-L     Document Type: Article
Times cited : (82)

References (30)
  • 1
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    • Ed.: A. Brossi. Academic Press, San Diego
    • For reviews, see a) Z.-J. Liu, R.-R. Lu in The Alkaloids, Vol. 33 (Ed.: A. Brossi). Academic Press, San Diego, 1988, pp. 83-140, and earlier reviews in this series;
    • (1988) The Alkaloids , vol.33 , pp. 83-140
    • Liu, Z.-J.1    Lu, R.-R.2
  • 14
    • 0345646422 scopus 로고
    • PhD thesis, University of California, Irvine (USA)
    • c) M. J. Sharp, PhD thesis, University of California, Irvine (USA), 1991.
    • (1991)
    • Sharp, M.J.1
  • 15
    • 0000499852 scopus 로고
    • Prepared in 92% yield from 3-methylanisole by the literature procedure: G. M. Rubottom, J. M. Gruber, J. Org. Chem. 1977, 42, 1051.
    • (1977) J. Org. Chem. , vol.42 , pp. 1051
    • Rubottom, G.M.1    Gruber, J.M.2
  • 17
    • 0344783787 scopus 로고
    • PhD thesis, University of California, Irvine (USA)
    • b) M. E. Okazaki, PhD thesis, University of California, Irvine (USA), 1986.
    • (1986)
    • Okazaki, M.E.1
  • 21
    • 0032139353 scopus 로고    scopus 로고
    • For the first use of an intramolecular Heck reaction to form the spirooxindole functionality of gelsemine, see ref. [Sb]. For recent reviews on the use of intramolecular Heck reactions in natural products total synthesis, see a) J. T. Link, L. E. Overman, CHEMTECH 1998, 28, 19;
    • (1998) CHEMTECH , vol.28 , pp. 19
    • Link, J.T.1    Overman, L.E.2
  • 23
    • 0026714767 scopus 로고
    • The high selectivity for the formation of 15a is attributed to the coordination of the angular vinyl group to the cationic palladium species during the insertion step, see A. Madin, L. E. Overman, Tetrahedron Lett. 1992, 33, 4859.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 4859
    • Madin, A.1    Overman, L.E.2
  • 24
    • 0344351809 scopus 로고    scopus 로고
    • note
    • The oxindole configuration was determined by nuclear overhauser enhancement (NOE) experiments. A positive NOE was observed between the hydrogen atoms on C9 and C19 of the major diastereomer 15a while the minor diastereomer 15b showed a positive NOE between the hydrogen atoms on C9, C5, and C16.
  • 29
    • 0345646421 scopus 로고    scopus 로고
    • note
    • N1 process, or by other possible mechanisms.
  • 30
    • 0345646420 scopus 로고    scopus 로고
    • note
    • 13C NMR, IR, and HR-MS analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.