Synthetic approaches towards phorbols via the ultra-high-pressure mediated intramolecular Diels–Alder reaction of furans (IMDAF): effect of furan substitution

Abstract

Tricyclic structures having the functionality and stereochemistry inherent in phorbol and its analogues may be rapidly constructed by an ultra-high pressure IMDAF reaction. The nature of the 2-thioether substituent on the furan diene is critical for the success of the key cycloaddition reaction.

References

1. R. Bohm, B. Flaschentrager and L. Lendle, Arch. Exp. Pathol. Pharmakol., 1935, 177, 212.
2. W. Hoppe, F. Brandl, I. Strell, M. Röhrl, I. Gassmann, E. Hecker, H. Bartsch, G. Kreibich and Ch. V. Szczepanski, Angew. Chem., Int. Ed. Engl., 1967, 6, 809.
3. L. Seghal and G. S. Paliwal, Bot. J. Linn. Soc., 1974, 68, 173.
4. J. L. Hartwell, Lloydia, 1969, 32, 153; J. M. Watt and M. G. Breyer-Brandwijk, The Medicinal and Poisonous Plants of Southern and Eastern Africa, 2nd edn., E. & S. Livingstone, Edinburgh, 1962, p. 395; Th. J. C. Up Hof, Dictionary of Economic Plants, H. R. Engelmann, London, 1959, p. 151; W. Dymock, C. J. H. Warden and D. Hooper, Pharmacographica Indica, vol. 1(iii), Hambard National Fondation, Karachi, Pakistan, 1890, p. 247(reprinted 1972); J. R. Ainslie, A List of Plants in Native Medicine in Nigeria, Institute paper no. 7, Oxford University, Oxford, England, 1937, p. 27.
5. S. von Reis Altschul, Drugs and Foods from Little Known Plants, Notes in Harvard University Herbaria, Harvard University Press, Boston, 1973, p. 143; R. N. Chopra, I. C. Chopra, K. L. Handa and L. D. Kapur, Indigenous Drugs of India, 2nd edn., H. N. Dhur & Sons, Calcutta, 1958; F. J. Evans, The British Herbal Pharmacopoeia, British Herbal Medical Association, London, 1976, p. 81; F. J. Evans, A. D. Kinghorn and R. J. Schmidt, Acta Pharmacol. Toxicol., 1975, 37, 250; K. Lampe and P. Fagerström, Plant Toxicity and Dermatitis, Williams & Wilkins, Baltimore, 1968; J. Kingsbury, Poisonous Plants of the United States and Canada, Prentice Hall, Eaglewood Cliffs, NJ, 1964.
6. British Pharmacopoeia, The Pharmaceutical Press, London, 1949.
7. R. Castagnou, R. Baudriment and J. Gauthier, Compt. Rend., 1965, 260, 4109.
8. H. Ohigashi, K. Kawazu, K. Koshimizu and T. Mitsui, Agric. Biol. Chem., 1972, 36, 2529.
9. W. R. Kelly and I. R. C. Bick, Res. Vet. Sci., 1976, 20, 311.
10. F. J. Evans and A. D. Kinghorn, Lloydia, 1975, 38, 363.
11. F. J. Evans, Naturally Occuring Phorbol Esters, CRC Press, USA, 1986.
12. K. R. Gustafson, J. H. Cardellina, J. B. McMahon, R. J. Gulakowski, J. Ishitoya, Z. Szallasi, N. E. Lewin, P. M. Blumberg, O. S. Weislow, J. A. Beutler Jr., R. W. Buckheit, G. M. Cragg, P. A. Cox, J. P. Bader and M. R. Boyd, J. Med. Chem., 1978, 35, 1992.
13. E. Hecker and R. Schmidt, Fortschr. Chem. Org. Naturst., 1974, 377.
14. J. G. Kidd and P. Rous, J. Exp. Med., 1938, 68, 529.
15. M. Castagna, Y. Takai, K. Kaibuchi, S. Kimihiko, U. Kikkawa and Y. Nishizuka, J. Biol. Chem., 1982, 13, 7847.
16. P. A. Wender, R. M. Keenan and H. Y. Lee, J. Am. Chem. Soc., 1987, 109, 4390; P. A. Wender, H. Kogen, H. Y. Lee, J. D. Junger, R. S. Wilheim and P. D. Williams, J. Am. Chem. Soc., 1989, 111, 8954; P. A. Wender, H. Kogen, H. Y. Lee, J. D. Junger, R. S. Wilheim and P. D. Williams, J. Am. Chem. Soc., 1989, 111, 8957.
17. P. A. Wender, K. D. Rice and M. E. Schnute, J. Am. Chem. Soc., 1997, 33, 7897.
18. P. A. Wender, C. L. Hilleman and M. J. Szymonifka, Tetrahedron Lett., 1980, 21, 2205; P. A. Wender and K. Brighty, Tetrahedron Lett., 1982, 29, 6741.
19. K. Shigeno, K. Ohne, T. Yamaguchi, H. Sasai and M. Shibasaki, Heterocycles, 1992, 33, 161; K. T. Shigeno, H. Sasai and M. Shibasaki, Tetrahedron Lett., 1992, 33, 4937; K. Sugita, K. Shigeno, C. F. Neville, H. Sasai and M. Shibasaki, Synlett, 1994, 325; R. Tokunoh, H. Tomiyama, M. Sodeska and M. Shibaski, Tetrahedron Lett., 1996, 37, 2449.
20. J. H. Rigby and P. Ch. Kierkus, J. Am. Chem. Soc., 1989, 111, 4125; J. H. Rigby, P. Ch. Kierkus and D. Head, Tetrahedron Lett., 1989, 30, 5073.
21. P. C. B. Page, D. C. Jennens, R. A. Porter and A. N. Baldock, Synlett, 1991, 472; P. C. B. Page and D. C. Jennens, J. Chem. Soc., Perkin Trans. 1, 1992, 2587; P. C. B. Page, D. C. Jennens and H. McFarland, Tetrahedron Lett., 1997, 38, 5395.
22. W. G. Dauben, J. Dinges and T. C. Smith, J. Org. Chem., 1993, 58, 7635.
23. M. C. McMills, L. Zhuang, D. L. Wright and W. Watt, Tetrahedron Lett., 1994, 35, 8311.
24. L. A. Paquette, D. R. Sauer, S. D. Edmondson and D. Friedrich, Tetrahedron, 1994, 50, 4071.
25. J. I. McLoughlin, R. Brahma, O. Campopiano and R. D. Little, Tetrahedron Lett., 1990, 31, 1377.
26. S. J. Burrell, A. E. Derome, M. S. Edenborough, L. M. Harwood and S. A. Leeming, Tetrahedron Lett., 1985, 26, 2229; L. M. Harwood, S. A. Leeming, N. S. Isaacs, G. Jones, J. Pickard, R. M. Thomas and D. Watkin, Tetrahedron Lett., 1988, 29, 5017; D. P. Dolata and L. M. Harwood, J. Am. Chem. Soc., 1992, 114, 10738.
27. N. S. Isaacs, L. M. Harwood and S. A. Leeming, unpublished results.
28. K. A. Parker and M. R. Adamchuk, Tetrahedron Lett., 1978, 19, 1685.
29. L. A. Van Royen and P. J. DeClercq, Synth. Commun., 1979, 9, 771.
30. L. M. Harwood, G. Jones, J. Pickard, R. M. Thomas and D. Watkin, Tetrahedron Lett., 1988, 5825.
31. B. A. Keay and P. W. Dibble, Tetrahedron Lett., 1989, 1045.
32. L. M. Harwood, G. Jones, J. Pickard, R. M. Thomas and D. Watkin, J. Chem. Soc., Chem. Commun., 1990, 605; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas and F. J. Witt, J. Chem. Soc., Chem. Commun., 1990, 608.
33. H. Kotsuki, Y. Mori, T. Ohtsuka, H. Nishizawa, M. Ochi and K. Matsuoka, Heterocycles, 1987, 26, 2347.
34. G. A. Kraus and P. Gottschalk, Tetrahedron Lett., 1983, 24, 2727.
35. L. M. Harwood, T. Ishikawa, H. Phillips and D. Watkin, J. Chem. Soc., Chem. Commun., 1991, 527.
36. E. Niwa, H. Aski, H. Tanaka, K. Munakata and M. Namiki, Chem. Ber, 1966, 99, 3215.
37. L. M. Harwood, P. Marais and S. West, unpublished results.
38. D. W. Knight and D. C. Rustidge, J. Chem. Soc., Perkin Trans. 1, 1981, 679.
39. H. Gilman and G. F. Wright, J. Am. Chem. Soc., 1933, 55, 3302.
40. Crystal data: C₂₆H₃₀O₆S, M= 470.56, orthorhombic, P2₁²₁²₁a= 8.911, b= 12.194, c= 22.46 Å, V= 2440 ų, Z= 4, D= 1.281 g cm^–3, F(000)= 1000, independent reflections were collected on a Marresearch Image Plate System. The structure was solved by direct methods and refined on F² using SHELX 86. Final R= 0.0781, weighted R= 0.2445. Full crystallographic details, excluding structure factor tables, have been deposited at the Cambridge Crystallographic Data Centre (CCDC). For details of the deposition scheme, see ‘Instructions for Authors’, J. Chem. Soc., Perkin Trans. 1, available via the RSC web page (http://www.rsc.org/authors). Any request to the CCDC for this material should quote the full literature citation and the reference number 207/302.
41. G. Majetich, A. J. Leigh and S. Condon, Tetrahedron Lett., 1991, 32, 605.
42. C. J. Kowalski, A. E. Weber and K. W. Fields, J. Org. Chem., 1982, 47, 5088.
43. A. B. Smith, S. J. Branca, M. A. Guaciaro, P. M. Wovkulich and A. Korn, Org. Synth., 1990, Coll Vol VII, 271.
44. A. Fadel, R. Yefsah and J. Salaün, Synthesis, 1987, 37.
45. R. A. Silverman and D. M. Burness, J. Org. Chem., 1968, 33, 1869.
46. D. M. Burness, Org. Synth., 1959, 39, 49.
47. R. Grigg, J. A. Knight and M. V. Sargent, J. Chem. Soc., 1966, 976.
48. D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 1991, 113, 7277.
49. R. E. Ireland and L. Lui, J. Org. Chem., 1993, 58, 2899.