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A stereospecific approach to diterpene alkaloids with a bridge across ring B

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Zusammenfassung

Die Herstellung eines Schlüsselprodukts für die Synthese von Alkaloiden des Songorin- und Delphinin-Typs wird beschrieben.

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References

  1. For a model study seeK. Wiesner andA. Philipp, Tetrahedron Lett.14, 1467 (1966).K. Wiesner, A. Philipp andPak-Tsun Ho, Tetrahedron Lett.10, 1209 (1968); andKarin Bjamer Birnbaum, K. Wiesner andPak-tsun Ho, Tetrahedron Lett.14, 1071 (1969).

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  2. Satisfactory spectral data (IR, NMR and mass) were obtained for all compounds reported. All crystalline compounds gave a correct elemental analysis. For brevity, only some spectral data of special significance are reported.

  3. The position of the methoxyl in3 was rigorously proved by conversion to 7-methoxy-l-naphtoic acid. A simpler and regiospecific synthesis of compounds of the type3 has been being worked out in our laboratory.

  4. W. J. Musliner andJ. W. Gates Jr., J. Am. chem. Soc.88, 4272 (1966).

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Author information

Authors and Affiliations

  1. Natural Products Research Center, University of New Brunswick, Fredericton, N.B., Canada

    K. Wiesner, Pak-Tsun Ho, D. Chang & J. F. Blount

  2. Hoffmann La Roche Company Inc., Nutley, New Jersey, USA

    K. Wiesner, Pak-Tsun Ho, D. Chang & J. F. Blount

Authors
  1. K. Wiesner
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  2. Pak-Tsun Ho
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  3. D. Chang
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  4. J. F. Blount
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Additional information

We wish to thank the Hoffmann La Roche Company Inc., Nutley, New Jersey, and specifically Dr.A. Brossi, not only for financial support but also for collaboration and help. Financial support by the National Research Council of Canada is gratefully acknowledged.

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Wiesner, K., Ho, PT., Chang, D. et al. A stereospecific approach to diterpene alkaloids with a bridge across ring B. Experientia 28, 766–767 (1972). https://doi.org/10.1007/BF01923115

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  • DOI: https://doi.org/10.1007/BF01923115

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