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Volumn 121, Issue 33, 1999, Pages 7702-7703

Direct stereo- and enantiocontrolled synthesis of vicinal stereogenic quaternary carbon centers. Total syntheses of meso- and (-)-chimonanthine and (+)-calycanthine [4]

Author keywords

[No Author keywords available]

Indexed keywords

CALYCANTHINE; CHIMONANTHINE; INDOLE ALKALOID; UNCLASSIFIED DRUG;

EID: 0033603864     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991714g     Document Type: Letter
Times cited : (197)

References (36)
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  • 4
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    • and earlier reviews in this series
    • Examples can be found, inter alia, in asymmetric syntheses of diterpenes. For recent reviews, see: (a) Hanson, J. R. Nat. Prod. Rep. 1999, 209-219, and earlier reviews in this series.
    • (1999) Nat. Prod. Rep. , pp. 209-219
    • Hanson, J.R.1
  • 5
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    • For a recent example of forming both quaternary centers by a sigmatropic rearrangement see: Lemieux, R. M.; Meyers, A. I. J. Am. Chem. Soc. 1998, 120, 5453-5457.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5453-5457
    • Lemieux, R.M.1    Meyers, A.I.2
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    • 0043288716 scopus 로고
    • Brossi, A., Ed.; Academic: San Diego
    • For recent reviews that briefly discuss this indole alkaloid family, see: (a) Hino, T.; Nakagawa, M. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 34, pp 1 -75.
    • (1989) The Alkaloids , vol.34 , pp. 1-75
    • Hino, T.1    Nakagawa, M.2
  • 7
    • 77957063766 scopus 로고
    • Brossi, A., Ed.; Academic: New York
    • (b) Wrobel, J. T. In The Alkaloids; Brossi, A., Ed.; Academic: New York, 1985; Vol. 26, pp 53-87.
    • (1985) The Alkaloids , vol.26 , pp. 53-87
    • Wrobel, J.T.1
  • 23
    • 0029790020 scopus 로고    scopus 로고
    • For the first stereocontrolled total synthesis of a 3a,3a′-bispyrro[2,3-b]indoline alkaloid, see: Link, J. T.; Overman, L. E. J. Am. Chem. Soc. 1996, 118, 8166-8167.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8166-8167
    • Link, J.T.1    Overman, L.E.2
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    • Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim; Chapter 6
    • For a recent review of the use of intramolecular Heck reactions in natural products total synthesis, see: Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim; 1998, Chapter 6.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions
    • Link, J.T.1    Overman, L.E.2
  • 29
    • 0344391697 scopus 로고    scopus 로고
    • note
    • (a) The stereochemistry of the siloxy substituent of 14 has not yet been established. (b) Due to slow conformational equilibration on the NMR time scale, NMR spectra of this intermediate are highly complex.
  • 30
    • 0345686193 scopus 로고    scopus 로고
    • note
    • The trans vicinal siloxy groups of 13 preferentially adopt diaxial orientations, while the oxygen substituents are locked diequatorial in 17.
  • 31
    • 0344823424 scopus 로고    scopus 로고
    • note
    • The authors have deposited coordinates for this compound with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
  • 32
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    • 10b
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    • note
    • 26
  • 36
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    • note
    • 11 using the coupled oscillator CD method.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.