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Volumn 69, Issue 25, 2004, Pages 8681-8693

Conjugate additions to phenylglycinol-derived unsaturated δ-lactams. Enantioselective synthesis of uleine alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

NEGATIVE IONS; PHENOLS; SULFUR; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

EID: 10044262177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0487101     Document Type: Article
Times cited : (63)

References (75)
  • 1
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    • Indoles. The monoterpenoid indole alkaloids
    • Saxton, J. E., Ed.; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, Chapter 6
    • (a) Joule, J. A. Indoles. The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, Chapter 6.
    • (1983) The Chemistry of Heterocyclic Compounds , vol.25 , Issue.PART 4
    • Joule, J.A.1
  • 2
    • 0000404240 scopus 로고
    • Monoterpenoid indole alkaloids
    • Saxton, J. E., Ed.; Taylor, E. C., Ed.; Wiley: Chichester, Part 4, Chapter 6
    • (b) Alvarez, M.; Joule, J. A. Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Suppl. to Vol. 25, Part 4, Chapter 6.
    • (1994) The Chemistry of Heterocyclic Compounds , vol.25 , Issue.SUPPL.
    • Alvarez, M.1    Joule, J.A.2
  • 3
    • 10044241331 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York, Chapter 4
    • (c) Alvarez, M.; Joule, J. A. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 2001; Vol. 57, Chapter 4.
    • (2001) The Alkaloids , vol.57
    • Alvarez, M.1    Joule, J.A.2
  • 5
    • 0013848559 scopus 로고
    • The biogenetic numbering is used throughout this paper for all tetracyclic compounds. Le Men, J.; Taylor, W. I. Experientia 1965, 21, 508.
    • (1965) Experientia , vol.21 , pp. 508
    • Le Men, J.1    Taylor, W.I.2
  • 38
    • 10044234801 scopus 로고    scopus 로고
    • note
    • In both cases, minor amounts of the respective C-16 epimer were also formed as a consequence of the epimerization occurring at the ester α carbon during the cyclization step.
  • 41
    • 10044241330 scopus 로고    scopus 로고
    • note
    • Molecular mechanics (MM.; CVFF91 force field) calculations provide support to this conclusion because they indicated that the exo adducts 4a and 6 are less stable that the corresponding C-7 epimers.
  • 42
    • 0141532310 scopus 로고    scopus 로고
    • For a recent review, see: Pellissier, H. Tetrahedron 2003, 59, 8291.
    • (2003) Tetrahedron , vol.59 , pp. 8291
    • Pellissier, H.1
  • 43
    • 10044276118 scopus 로고    scopus 로고
    • note
    • According to MM calculations, the endo adducts 11a, 24b, 28b, and 33b were more stable than the respective exo epimers.
  • 46
    • 0043206066 scopus 로고    scopus 로고
    • For a recent review on 1,3-dithianes in natural product synthesis, see: Yus, M.; Nájera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
    • (2003) Tetrahedron , vol.59 , pp. 6147
    • Yus, M.1    Nájera, C.2    Foubelo, F.3
  • 62
    • 10044282451 scopus 로고    scopus 로고
    • note
    • For a related cyclization, see ref 10n.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.