Convergent total synthesis of lamellarin K†

(Note: The full text of this document is currently only available in the PDF Version )

Martin Banwell and David Hockless


The azomethine ylide derived from dihydroisoquinolinium salt 24 undergoes an intramolecular [3 + 2] cycloaddition reaction to give pyrrole 25 which upon de-isopropylation affords the marine alkaloid lamellarin K 4.


References

  1. R. J. Andersen, D. J. Faulkner, H. Cun-heng, G. D. Van Duyne and J. Clardy, J. Am. Chem. Soc., 1985, 107, 5492 CrossRef CAS.
  2. N. Lindquist, W. Fenical, G. D. Van Duyne and J. Clardy, J. Org. Chem., 1988, 53, 4570 CrossRef CAS.
  3. A. R. Carroll, B. F. Bowden and J. C. Coll, Aust. J. Chem., 1993, 46, 489 CAS.
  4. S. Urban and R. J. Capon, Aust. J. Chem., 1996, 49, 711 CAS.
  5. M. Venkata Rami Reddy, D. J. Faulkner, Y. Venkateswarlu and M. Rama Rao, Tetrahedron, 1997, 53, 3457 CrossRef CAS.
  6. A. R. Quesada, M. D. García Grávalos and J. L. Fernández Puentes, Br. J. Cancer, 1996, 74, 677 CAS; J. L. Fernández Puentes, D. García Grávalos and A. Quesada, PCT Int. Appl., WO 9701336 (Chem. Abstr., 1996, 126, 166 474) Search PubMed.
  7. A. Heim, A. Terpin and W. Steglich, Angew. Chem., 1997, 109, 158; Angew. Chem., Int. Ed. Engl., 1997, 36, 155 Search PubMed.
  8. F. Ishibashi, Y. Miyazaki and M. Iwao, Tetrahedron, 1997, 53, 5951 CrossRef CAS.
  9. For reviews on azomethine ylide chemistry see: R. Grigg, Chem. Soc. Rev., 1987, 16, 89 Search PubMed; O. Tsuge and S. Kanemasa, Adv. Heterocycl. Chem., 1989, 45, 232 RSC; A. Padwa, in Comprehensive Organic Synthesis, Vol. 4, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, pp. 1085–1089; P. A. Wade, in Comprehensive Organic Synthesis, Vol. 4, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, pp. 1134–1141.
  10. For a review see K. Sonogashira, in Comprehensive Organic Synthesis, Vol. 3, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, pp. 521–549 Search PubMed.
  11. A. Arcadi, S. Cacchi, M. D. Rosario, G. Fabrizi and F. Marinelli, J. Org. Chem., 1996, 61, 9280 CrossRef CAS.
  12. M. F. Comber and M. V. Sargent, J. Chem. Soc., Perkin Trans. 1, 1991, 2783 RSC.
  13. T. Sala and M. V. Sargent, J. Chem. Soc., Perkin Trans. 1, 1979, 2593 RSC.
  14. E. J. Corey and P. L. Fuchs, Tetrahedron Lett., 1972, 3769 CrossRef CAS.
  15. H. Ishii, I.-S. Chen and T. Ishikawa, J. Chem. Soc., Perkin Trans. 1, 1987, 671 RSC.