Cyclization of 1,5-dienes: An efficient synthesis of β-Georgywood

Journal of Organic Chemistry

Volumn 72, Issue 4, 2007, Pages 1112-1120

  Fráter, Georg ^a   Schröder, Fridtjof ^a  

^a GIVAUDAN SCHWEIZ AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL GROUP; CYCLIZATION REACTIONS; LEWIS ACIDS;

CATALYSIS; CHEMICAL BONDS; ISOMERIZATION; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

OLEFINS;

ALKADIENE; ALUMINUM CHLORIDE; ALUMINUM DERIVATIVE; BETA GEORGYWOOD; BRONSTED ACID; CARBONYL DERIVATIVE; CYCLOHEXENE DERIVATIVE; LEWIS ACID; METHYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION;

EID: 33846976722     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061668k     Document Type: Article

References (71)

1. Parts of this investigation were presented at the 11th International Conference of Organic Process Research & Development, Barcelona, Spain, April 25-28, 2005, and at the XVI Fechem Conference on Organometallic Chemistry, Budapest, Hungary, September 3-8, 2005.
2. (a) Eschenmoser, A.; Arigoni, D. Helv. Chim. Acta 2005, 88, 3011-3354.
3. (b) Stork, G.; Burgstahler, A. W. J. Am. Chem. Soc. 1955, 77, 5068-5077 and literature cited therein,
4. (c) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890-1904 and literature cited therein.
5. Tiemann, F.; Krüger, P.; Semmler, F. H. Ber. Dtsch. Chem. Ges. 1893, 26, 2675-2729.
6. (a) Johnson, W. S. Angew. Chem., Int. Ed. Engl. 1976, 15, 9-17.
7. (b) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1982; Vol. III, pp 341-409.
8. (c) Gnonlonfoun, N. Bull. Chem. Soc. Fr. 1988, 862-869.
9. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163.
10. (e) De la Torre, M. C.; Sierra, M. A. Angew. Chem., Int. Ed. 2004, 43, 160-181.
11. (f) Yoder, R. A.; Johnston, J. N. Chem. Rev. 2005, 105, 4730-4756.
12. (a) Ohloff, G. Riechstoffe Aromen 1957, 38-40.
13. (b) Ohloff, G. DE 1057108, 1957, Dragoco Spezialfabrik konz. Riech- und Aromastoffe Gerberding & Co., G.m.b.H. [Chem. Abstr. 55, 48611].
14. (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633-7703.
15. (b) Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Angew. Chem., Int. Ed. 2000, 39, 2980-3010.
16. (c) Gautschi, M.; Bajgrowicz, J. A.; Kraft, P. Chimia 2001, 55, 379-387.
17. Etzweiler, F.; Helmlinger, D.; Nussbaumer, C.; Pesaro, M. EP 0464357, priority 2.6.1990 to Givaudan [Chem. Abstr. 116, 194638w].
18. See also: Nussbaumer, C.; Fráter, G.; Kraft, P. Helv. Chim. Acta 1999, 82, 1016-1024.
19. Mousseron-Canet, M.; Mousseron, M.; Boch, J. J. Bull. Chem. Soc. Chim. Fr. 1959, 601-606.
20. Bajgrowicz, J; Bringhen, A; Fráter, G; Müller, U. EP 0743297, priority 16.5.1995 to Givaudan [Chem. Abstr. 126, 103856h].
21. (a) Erman, M. B.; Hoffmann, H. M.; Cardenas, C. G. EP 0985651, priority 16.8.1998 to Millenium Speciality Chemicals, Inc. [Chem. Abstr. 132, 207981k].
22. (b) Erman, M. B.; Williams, M. J.; Cardenas, C. G. WO 200160777, priority 18.2.2000 to Millenium Speciality Chemicals, Inc. [Chem. Abstr. 135, 197197e].
23. (c) Erman, M. B.; Williams, M. J.; Whelan, P.; Cardenas, C. G.; Antipin, M. Perfum. Flavor. 2001, 26, 18-21.
24. Bella, M.; Cianflone, M.; Montemurro, G.; Passacantilli, G.; Piancatelli, G. Tetrahedron 2004, 60, 4821-4827.
25. (a) Fráter, G.; Müller, U.; Nussbaumer, C. Book of Abstracts; 213th National Meeting of the American Chemical Society, San Francisco, April 13-17, 1997; American Chemical Society: Washington, D.C., 1997.
26. (b) Fráter, G.; Müller, U.; Schröder, F. Tetrahedron: Asymmetry 2004, 15, 3967-3972.
27. Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 1346-1352.
28. Barras, J.-P.; Schröder, F. WO 2005016938, priority 18.8.2003 to Givaudan [Chem. Abstr. 142, 219409z].
29. (a) Stadler, P. A.; Nechvatal, A.; Frey, A. J; Eschenmoser, A. Helv. Chim. Acta 1957, 40, 1373-1490.
30. (b) Stadler, P. A.; Eschenmoser, A.; Schinz, H.; Stork, G. Helv. Chim. Acta 1957, 40, 2191-2198.
31. (c) Eschenmoser, A.; Felix, D.; Gut, M.; Meier, J.; Stadler, P. in CIBA Foundation Symposium on the Biosynthesis of Terpenes and Steroids; Wolstenholme, G. E. W., O'Connor, M., Eds.; J. & A. Churchill: London, UK, 1959; p 217.
32. (a) Kron, A. A.; Burdin, E. A.; Fedotova, Z. M.; Novikov, N. A. Russ. J. Org. Chem. 1994, 30, 1035-1038.
33. (b) Andreev, V. M.; Cherkaev, G. V.; Ratnikova, E. V.; Andreeva, L. K.; Formchenko, Z. V. Zh. Org. Khim. 1991, 27, 413-414.
34. (a) Baldwin, J. E.; Lusch, M. J. J. Org. Chem. 1979, 44, 1923-1927.
35. ( b) Snider, B. B.; Cartaya-Marin, C. P. J. Org. Chem. 1984, 49, 153-157.
36. (a) Markovnikov addition of formic acid to trisubstituted double bonds and re-elimination: Baird, K. J.; Grundon, M. F.; Harrison, D. M.; Magee, M. G. Heterocycles 1981, 713-717.
37. (b) Addition of phosphoric acid: Julia, M.; Mestdagh, H.; Rolando, C. Tetrahedron 1986, 42, 3841-3849. HX addition and re-elimination was observed by us when bubbling HCl or HBr through precursor 5 (GC/MS), where after attempted isolation of these halides the partially isomerized mixtures 7, 8 were obtained after chromatography or distillation.
38. This hypothesis represents so far the best answer to the important question, why Brønsted acids induce preisomerization and strong, active LA's do not. We also considered an inductive deactivation of the cyclohexenyl double bond depending on the strength of the carbonyl group/acid complex. Although we could not find a well-proven precedent for a deactivation over three σ-bonds, such an effect cannot be excluded.
39. (a) Zhang, J.-H.; Wang, M.-X.; Huang, Z.-T. J. Chem. Soc., Perkin Trans. 1 1999, 2087-2094.
40. (b) Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: New York, 2005.
41. Baddeley, G.; Heaton, B. G; Rasburn, J. W. J. Chem. Soc. 1960, 4713-4719. As in our case (12, 15) the formation of an endocyclic enol ether was not possible, due to the fully substituted endocyclic α-position.
42. Brandt, J.; Hoffmann, E. G. Brennst. Chem. 1964, 7, 200-206.
43. (a) Pearson, R. G. Hard and Soft Acids and Bases. J. Am. Chem. Soc. 1962, 85, 3533-3539.
44. (b) Santelli, M.; Pons, J.-M. Lewis acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, FL, 1996.
45. Olah, G. A.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc. 1972, 94, 7448-7461.
46. Kobayashi, S.; Busujima, T.; Nagayama, S. Chem. Eur. J. 2000, 6, 3491-3494.
47. Pasedach, H. DE 2228333, BASF, 1972 [Chem. Abstr. 142, 219409z].
48. Alkynol 26 also can be prepared from Dehydro-β-linalol (CAS 29171-20.-8) by using the 3-step procedure described by Glänzer: Glänzer, B. I.; Faber, K.; Griengl, H. Tetrahedron 1978, 43, 5791-5796.
49. Damm, L. G.; Hartshorn, M. P.; Vaughan, J. Aust. J. Chem. 1976, 29, 1017-1021.
50. We cannot exclude that backside shielding of the α-face of 25 by the isohexenyl side chain, probably favored by π-stacking (in analogy to Figure 3), is solely responsible for this preference.
51. 3.
52. a units: (a) Yamamoto, H.; Futatsugi, K. Angew. Chem., Int. Ed. 2005, 44, 1924-1942.
53. (b) Ren, H.; Cramer, C. J.; Squires, R. R. J. Am. Chem. Soc. 1999, 121, 2633-2634.
54. Anet F L.; O'Leary, D. J. Tetrahedron Lett. 1989, 30, 2755-2758.
55. 2 have also been used successfully in reactions such as Cycloalkylation, intramolecular Diels-Alder, epoxide-initiated cation-olefin cyclization, aldol condensation, carbocationic cyclization of unsaturated carbonyl compounds, and carbonyl ene reactions. See, for example: (a) Abouabdellah, A.; Bonnet-Delpon, D. Tetrahedron 1994, 50 11921-11932.
56. (b) Rogers C.; Keay, B. Can. J. Chem. 1993, 71, 611-622.
57. (c) Corey, E. J.; Sodeoka, M. Tetrahedron Lett. 1991, 32, 7005-7008.
58. (d) Naruse, Y.; Ukai, J.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1985, 1451-1452.
59. (e) Goeke, A.; Mertl, D.; Brunner, G. Angew. Chem., Int. Ed. 2004, 44, 99-101.
60. (a) Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett 1999, 40, 4457-4460.
61. (b) Evans, D. A.; Chapman, K. T.; Bisaha J. J. Am Chem. Soc. 1988, 110, 1238-1256.
62. (a) Snider, B. B.; Cartaya-Marin, C. P. J. Org. Chem. 1984, 49, 153-157.
63. (b) Snider, B. B.; Karras, M.; Price, R. T.; Rodini, D. J. J. Org Chem. 1982, 47, 4538-4545.
64. (c) Karras, M.; Snider, B. B. J. Am. Chem Soc. 1980, 102, 7951-7953.
65. (d) Snider, B. B.; Rodini, D. J.; van Straten J. J. Am. Chem. Soc. 1980, 102, 5872-5880. See also ref 32e.
66. (a) Lehmkuhl, H.; Ziegler, K. In Houben-Weyl, Methoden der organischen Chemie; Müller, E., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1970; pp 51-55, 59-78, and 95-101 and refs 2-5 on p 71
67. (b) Tarao, R.; Takeda, S. Bull Chem. Soc. Jpn. 1967, 40, 650-655.
68. (c) Lehmkuhl, H.; Kobs, H. D. Tetrahedron Lett. 1965, 29, 2505-2510.
69. Starowieyski, K. B.; Pasynkiewicz, S.; Sporzynski, A. J Organomet Chem. 1976, 117, 117-128.
70. See, for example: Smith, C. A.; Wallbridge, G. H. J. Chem Soc A 1967, 7-12.
71. Inukai, T.; Michio, K. J. Org. Chem. 1965, 30, 3567-3569.