Total syntheses of palmarumycins CP1 and CP2 and CJ-12,371: novel spiro-ketal fungal metabolites

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Anthony G. M. Barrett and Thorsten Meyer


Abstract

Total syntheses of palmarumycins CP1 1 and CP2 9 and the structurally related CJ-12,371 11 are reported, thereby establishing a strategy for the synthesis of further natural products in the palmarumycins, diepoxines and preussomerines family.


References

  1. K. Krohn, A. Michel, U. Flörke, H.-J. Aust, S. Draeger and B. Schulz, Liebigs Ann. Chem., 1994, 1093 Search PubMed; 1994, 1099.
  2. G. Schlingmann, R. R. West, L. Milne, C. J. Pearce and G. T. Carter, Tetrahedron Lett., 1993, 34, 7225 CrossRef CAS; F. Petersen, T. Moerker, F. Vanzanella and H. H. Peter, J. Antibiot., 1994, 47, 1098 CAS; R. Thiergardt, P. Hug, G. Rihs and H. H. Peter, Tetrahedron Lett., 1994, 35, 1043 CrossRef CAS; Tetrahedron, 1995, 51, 733 Search PubMed.
  3. H. A. Weber, N. C. Baezinger and J. B. Gloer, J. Am. Chem. Soc., 1990, 112, 6718 CrossRef CAS; H. A. Weber and J. B. Gloer, J. Org. Chem., 1991, 56, 4355 CrossRef CAS; S. B. Singh, D. L. Zink, J. M. Liesch, R. G. Ball, M. A. Goetz, E. A. Bolessa, R. A. Giacobbe, K. C. Silverman, G. F. Bills, F. Pelaez, C. Cascales, J. B. Gibbs and R. B. Lingham, J. Org. Chem., 1994, 59, 6296 CrossRef CAS.
  4. M. Chu, I. Truumees, M. G. Patel, V. P. Gullo and M. S. Puar, J. Org. Chem., 1994, 59, 1222 CrossRef CAS; M. Chu, I. Truumees, M. G. Patel, V. P. Gullo, C. Blood, I. King, J.-K. Pai and M. S. Puar, Tetrahedron Lett., 1994, 35, 1343 CrossRef CAS; M. Chu, I. Truumees, M. G. Patel, C. Blood, P. R. Das and M. S. Puar, J. Antibiot., 1995, 48, 329 CAS; M. Chu, M. G. Patel, J.-K. Pai, P. R. Das and M. S. Puar, Biorg. Chem. Lett., 1996, 6, 579 Search PubMed; G. Schlingmann, S. Matile, N. Berova, K. Nakanishi and G. T. Carter, Tetrahedron, 1996, 52, 435 CrossRef CAS; G. Bringmann, S. Busemann, K. Krohn and K. Beckmann, Tetrahedron, 1997, 53, 1655 CrossRef CAS; K. Krohn, K. Beckmann, U. Flörke, H.-J. Aust, S. Draeger, B. Schulz, S. Busemann and G. Bringmann, Tetrahedron, 1997, 53, 3101 CrossRef CAS.
  5. P. Wipf and J.-K. Jung, Angew. Chem., Int. Ed. Engl., 1997, 36, 764 CrossRef CAS.
  6. K. Krohn, K. Beckmann, H.-J. Aust, S. Draeger, B. Schulz, S. Busemann and G. Bringmann, Liebig Ann. Recl., 1997, 2531 Search PubMed.
  7. H. Erdmann, Ann. Chem., 1888, 247, 356 Search PubMed.
  8. For examples of benzylic oxidations using chromium reagents, see: N. Chidambaram and S. Chandrasekaran, J. Org. Chem., 1987, 52, 5048 Search PubMed; R. Rathore, N. Saxena and S. Chandrasekaran, Synth. Comm., 1986, 16, 1493 CrossRef CAS; J. Muzart, Tetrahedron Lett., 1987, 28, 2131 CAS; R. Rangarajan and E. J. Eisenbraun, J. Org. Chem., 1985, 50, 2435 CrossRef CAS; B. M. Choudary, A. D. Prasad, V. Bhuma and V. Swapna, J. Org. Chem., 1992, 57, 5841 CrossRef CAS.
  9. B. W. Bycroft and J. C. Roberts, J. Chem. Soc., 1963, 4868 RSC.
  10. M. V. Bhatt and S. U. Kulkarni, Synthesis, 1983, 249 CrossRef CAS.
  11. D. R. Buckle, in Reagents for Organic Synthesis, Wiley, Chichester 1995, vol. 3, p. 1699 Search PubMed.
  12. P. F. King and S. G. Stroud, Tetrahedron Lett., 1985, 26, 1415 CrossRef CAS.
  13. P. V. Ramachandran, B. Gong and H. C. Brown, Tetrahedron Lett., 1994, 35, 2141 CrossRef CAS.
  14. S. Sakemi, T. Inagaki, K. Kaneda, H. Hirai, E. Iwata, T. Sakakibara, Y. Yamauchi, M. Norcia, L. M. Wondrack, J. A. Sutcliffe and N. Kojima, J. Antibiot., 1995, 48, 134 CAS.
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