Synthesis of bridged nine-membered ring ethers: Studies directed towards the synthesis of eunicellin-based marine diterpenes

Tetrahedron

Volumn 53, Issue 12, 1997, Pages 4331-4338

  Nowakowski, M ^a,b   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; MACROCYCLIC COMPOUND;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; THEORY;

EID: 0031585088     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00152-X     Document Type: Article

References (46)

1. 1. a) Faulkner, D. J. Nat. Prod. Rep. 1984, 551. Marine Natural Products: Metabolites of Marine Invertebrates.
2. b) Connolly, J. D., Hill, R. A. Eds. Dictionary of Terpenoids, Vol. 2, Chapman & Hall, London, 1991.
3. c) Newman, A. A. Ed. Chemistry of Terpenes and Terpenoids, Academic Press, London, 1991.
4. d) Faulkner, D. J. Nat. Prod. Rep. 1993, 497. Marine Natural Products.
5. 2. a) Ibers, J. A. Acta Crystallogr. 1961, 14, 1001.
6. b) Weinheimer, A. J.; Chang, C. W. J.; Matson, J. A. Naturally Occurring Cembranes in Herz, W.; Grisebach, H., Kirby, G. W. Eds. Progr. Chem. Org. Nat. Prod. 1979, 36, 285.
7. c) Tius, M. A. Chem. Rev. 1988, 88, 719.
8. d) Nishitani, K.; Konomi, T.; Mimaki, Y.; Tsunoda, T.; Yamakawa, K. Heterocycles 1993, 36, 1957.
9. 3. a) Kennard, O.; Watson, D. G.; Riva di Sanseverino, L.; Tursch, B.; Bosmans, R.; Djerassi, C. Tetrahedron Lett. 1968, 2879.
10. b) Uchio, Y.; Kodama, M.; Usui, S.; Fukazawa, Y. Tetrahedron Lett. 1992, 33, 1317.
11. c) Ortega, M. J.; Zubia, E.; He, H.-Y.; Salvá, J. Tetrahedron 1993, 49, 7823.
12. 4 a) Stierle, D. B.; Carté, B.; Faulkner, D. J.; Tagle, B.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 5088.
13. b) Rodriguez, A. D.; Cóbar, O. M. Tetrahedron 1993, 49, 319.
14. 5 Lin, Y.; Bewley, C. A.; Faulkner, D. J. Tetrahedron 1993, 49, 7977.
15. 6 van Boeckl, C. A. A.; Eklund, A. M.; Petitou, M.; Wahlberg, I. Cyclized Cembranoids of Natural Occurrence, in Herz, W.; Kirby, G. W.; Moore, R. E.; Steglich, W.; Tamm, Ch. Eds. Progr. Chem. Org. Nal. Prod. 1992, 60, 1.
16. 7 a) Coll, J. C. Chem. Rev. 1992, 92, 613.
17. b) Pawlik, J. R. Chem. Rev. 1993, 93, 1911.
18. 8 Recently a synthesis of eunicellin diterpenoids based on a Nozaki-Utimoto-Kishi Cr(II)/Ni(II)-mediated formation of the central nine-membered ring has been reported. L. E. Overman, lecture held at the Scientific Symposium on the occasion of the centennial celebrations 700 Jahre Chemisch Wissenschaftliches Laboratorium der BAYER AG in Wuppertal-Elberfeld 1896-1996' (Oct. 1996).
19. 9. For recent reviews of ring enlargement strategies for the synthesis of medium sized rings see: a) Paquette, L. A. Chem. Soc. Rev. 1995, 9.
20. b) Tochtermann, W.; Kraft, P. Synlett 1996, 1029.
21. c) Roxburgh, C. J. Tetrahedron 1993, 49, 10749.
22. 10. Illuminati, G.; Mandolini, L. Acc. Chem. Res 1981, 14, 95.
23. 11. Moody, C. J.; Davies, M. J. Stud. Nat. Prod. Chem. 1992, 10, 201.
24. 12. a) Hoffmann, H. M. R.; Brandes, A. Tetrahedron 1995, 51, 155.
25. b) Nicolaou, K. C.; Veale, C. A.; Hwang, C.-K.; Hutchinson, J.; Prasad, C. V. C.; Ogilvie, W. W. Angew. Chem. 1991, 103, 304; Angew. Chem. Int. Ed. 1991, 30, 299.
26. b) Nicolaou, K. C.; Veale, C. A.; Hwang, C.-K.; Hutchinson, J.; Prasad, C. V. C.; Ogilvie, W. W. Angew. Chem. 1991, 103, 304; Angew. Chem. Int. Ed. 1991, 30, 299.
27. c) Schreiber, S. L.; Kelly, S. E. Tetrahedron Lett. 1984, 25, 1757.
28. 13. a) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E.; Reddy, K. B. Tetrahedron Lett. 1987, 28, 1501.
29. b) Oh, J.; Lee, J.; Jin, S.-J.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3449.
30. c) Beer, T. Diss. University of Hannover 1995.
31. d) Oishi, T.; Shoji, M.; Maeda, K.; Kumahara, N.; Hirama, M. Synlett 1996, 1165.
32. 14. a) Carling, R. W.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1986, 565.
33. b) Paquette, L. A.; Sweeney, T. J. J. Org. Chem. 1990, 55, 1703.
34. c) Stohrer, I. Diss. University of Hannover 1992.
35. 15. a) Ashcroft, M. R.; Hoffmann, H. M. R. Org. Synth., Coll. Vol. 6, 512, 1988.
36. b) Hoffmann, H. M. R. in Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A. Ed., Wiley, Chichester 1995.
37. 16. a) Winterfeldt, E. Prinzipien und Methoden der Stereoselektiven Synthese, Vieweg, Braunschweig/Wiesbaden, 1988.
38. b) Stohrer, I.; Hoffmann, H. M. R. Helv. Chim. Acta 1993, 76, 2194.
39. 17. Rubinger, M. M. M.; Mann, J.; Drew, M. G. B. Tetrahedron 1995, 51, 11295.
40. 18. For an excellent survey of lanthanide reagents in organic synthesis see: Molander, G. A. Chem. Rev. 1992, 92, 29, see also Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693 and subsequent papers.
41. 18. For an excellent survey of lanthanide reagents in organic synthesis see: Molander, G. A. Chem. Rev. 1992, 92, 29, see also Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693 and subsequent papers.
42. 19. Molander, G. A.; Etter, J. B. J. Org. Chem. 1986, 51, 1778.
43. 1H-NMR chemical shifts of the C(12) (δ = 0.90 ppm) and the C(13) (δ = O.89 ppm) methyl groups are nearly identical, suggesting that both methyl groups adopt an equatorial position.
44. 21 Balasubramanian, V.; Robinson, C. H. Tetrahedron Lett. 1981, 22, 501.
45. 22 MMX-calculations were performed with the programme HYPER CHEM 30' from Microsoft on a standard PC and are based on 'force field theory'.
46. 23. Due to conformational flexibility of medium sized rings, NOE experiments do not seem to be very promising for elucidating the stereochemical scenario