Routes for the synthesis of (2S)-2-methyltetrahydropyran-4-one from simple optically pure building blocks

Organic Process Research and Development

Volumn 14, Issue 1, 2010, Pages 58-71

  Anderson, Kevin R ^a   Atkinson, Stéphanie L G ^a   Fujiwara, Takahiro ^b   Giles, Melvyn E ^a   Matsumoto, Takaji ^b   Merifield, Eric ^a   Singleton, John T ^a   Saito, Takao ^b   Sotoguchi, Tsukasa ^b   Tornos, James A ^a,c   Way, Edward L ^a  

^a ASTRAZENECA   (United Kingdom)

^b TAKASAGO INTERNATIONAL CORPORATION   (Japan)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77149132445     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900163a     Document Type: Article

References (56)

1. Bird, T. G. C.; Ple, P.; Crawley, G. C.; Large, M. S. Preparation of 4-aryl-4-hydroxy-tetrahydropyrans and 3-aryl-3-hydroxy-tetrahydro- furans as 5-lipoxygenase inhibitors. EP 623614 A1, 1994.
2. Alcaraz, M.-L.; et al. Org. Process Res. Dev. 2005, 9, 555.
3. Crawley, G. C.; Briggs, M. T.; Dowell, R. I.; Edwards, P. N.; Hamilton, P. M.; Kingston, J. F.; Oldham, K.; Waterson, D.; Whalley, D. P. J. Med. Chem. 1993, 36, 295.
4. Crawley, G. C.; Briggs, M. T. J. Org. Chem 1995, 60, 4264.
5. Haslegrave, J. A.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4666.
6. Holt, R. A.; Rigby, S. R.; Waterson, D. Production of optically active 2-substituted tetrahydropyran-4-ones. WO 9719185 A1, 1997.
7. Hanschke, E. Chem. Ber. 1955, 88, 1053.
8. The synthesis of pyranol 6 by an intramolecular Prins cyclisation between 3-buten-1-ol and acetaldehyde is reversible and can go back either to the same starting materials or to formaldehyde and 4-penten- 2-ol. The latter will undergo a Prins reaction with acetaldehyde to generate 2,6-dimethylpyran-4-ol which remains essentially unreacted in the resolution step.
9. Mitsuda, M.; Hasegawa, J. Stereoselective preparation of 2-hydro- carbyl-2,3-dihydro-4H-pyran-4-ones. GB 2304339 A1, 1997.
10. Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. J. Am. Chem. Soc. 2005, 727, 1336.
11. See for example: Chaladaj, W.; Kwiatkowski, P.; Jurczak, J. Tetrahedron Lett. 2008, 49, 6810.
12. Du, H.; Zhang, X.; Wang, Z.; Bao, H.; You, T; Ding, K. Eur. J. Org. Chem. 2008, 2248.
13. Wang, Y.; Wolf, J.; Zavalij, P.; Doyle, M. P. Angew. Chem., Int. Ed. 2008, 47, 1439.
14. Seki, K.; Ueno, M.; Kobayashi, S. Org. Biomol. Chem. 2007, 5, 1347.
15. Berkessel, A.; Vogl, N. Eur. J. Org. Chem. 2006, 5029.
16. Du, H.; Zhang, X.; Wang, Z.; Ding, K. Tetrahedron 2005, 61, 9465.
17. Anada, M.; Washio, T.; Shimada, N.; Kitagaki, S.; Nakajima, M.; Shiro, M.; Hashimoto, S. Angew. Chem., Int. Ed. 2004, 43, 2665.
18. A Ru-BINAP catalyst can be used for the preparation of methyl (S)- hydroxybutyrate 36 from methyl acetoacetate; see: Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Organic Syntheses; Wiley & Sons: New York, 1998;
19. Collect. Vol. 9, p 589.
20. SEGPHOS, however, was used as ligand in place of BINAP since it gives better results for reduction of β-keto esters: Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
21. Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405.
22. Huck, W.-R.; Burgi, T.; Mallat, T.; Baiker, A. J. Catal. 2001, 200, 171.
23. Fehr, M. J.; Consiglio, G.; Scalone, M.; Schmid, R. J. Org. Chem. 1999, 64, 5768.
24. Sato, M.; Sakaki, J.; Sugita, Y.; Nakano, T.; Kaneko, C. Tetrahedron Lett. 1990, 31, 7463.
25. Tamarez, M. M.; Franck, R. W.; Geer, A. Tetrahedron 2003, 59, 4249.
26. On a kilogram scale, lactone 17 was prepared from methyl-(S)- hydroxybutyrate by conversion to methyl-(S)-3-oxo-5-(tetrahydropy- ran-2-yloxy)hexanoate using methods developed from a published synthesis. Liu, L.; Tanke, R. S.; Miller, M. J. J. Org. Chem. 1986, 51, 5332. followed by acid-catalysed cyclisation to (S)-6-methyl-5,6- dihydropyran-2,4-dione and subsequent carbonyl protection.
27. Deschenaux, P.-F.; Kallimpoulos, T.; Stoeckli-Evans, H.; Jacot-Guillarmod, A. Helv. Chim. Acta 1989, 72, 731.
28. Drochner, D.; Müller, M. Eur. J. Org. Chem. 2001, 211.
29. Zipp, G. G.; Hilfiker, M. A.; Nelson, S. G. Org. Lett. 2002, 4, 1823.
30. Marques-Lopex, E.; Herrera, R. P.; Fernandez, R.; Lassaletta, J. M. Eur. J. Org. Chem. 2008, 3457.
31. Prandi, C.; Venturello, P. J. Org. Chem. 1994, 59, 3494.
32. Reiter, M.; Turner, H.; Gouverneur, V. Chem.-Eur. J. 2006,12, 7190.
33. Baker-Glenn, C.; Hodnett, N.; Reitner, M.; Ropp, S.; Ancliff, R.; Gouverneur, V. J. Am. Chem. Soc. 2005, 127, 1481.
34. Atkinson, S.; Tornos, J. Preparation of Optically Active Pyranone Derivatives. WO 2003051862 A1, 2003.
35. Sibi, M. P. Org. Prep. Proced. Int. 1993, 25,15.
36. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
37. Colle, S.; Taillefumier, C.; Chapleur, Y; Liebl, R.; Schmidt, A. Bioorg. Med. Chem. 1999, 7, 1049.
38. Hodgetts, K. J. Tetrahedron Lett. 2001, 42, 3763.
39. Gebauer, J.; Rost, D.; Blechert, S. Heterocvcles 2006, 68, 2129.
40. Prior studies on the racemic version of 23 demonstrated that the yield was compromised by formation of the product of aza-Michael addition of N-methoxymethylamine to the newly formed enone system 29. Investigation into the formation of this impurity demonstrated that it was formed during work-up, and by careful control of temperature and addition rate of the reaction quench this impurity could be minimised to less than 5%. Use of more acidic quench conditions was expected to suppress the formation of the impurity but led to some deprotection.
41. Reiter, M.; Ropp, S.; Gouverneur, V. Org. Lett. 2004, 6, 91.
42. Reiter, M.; Turner, H.; Mills-Webb, R.; Gouverneur, V. J. Org. Chem. 2005, 70, 8478.
43. 3 was found to give slightly better selectivity for pyranone 4 over pyranols 6a/6b, but the rate of reaction was slower.
44. Olah, G. A.; Prakash, G. K. S.; Arvanaghi, M. Synthesis 1984, 228.
45. Cohen, F.; Overman, L. E. J. Am. Chem. Soc. 2006, 128, 2594.
46. Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1968, 87, 916.
47. Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1968, 87, 1179.
48. Tius, M. A. 1-Methoxyallenyllithium. In e-EROS: Encyclopedia of Reagents for Organic Synthesis; Wiley: New York, 2001.
49. See for example: Weiberth, F. J.; Hall, S. S. J. Org. Chem. 1985, 50, 5308.
50. Perez, M.; Canoa, P.; Gomez, G.; Teijeira, M.; Fall, Y. Synthesis 2005, 411.
51. Chengebroyen, J.; Linke, M.; Robitzer, M.; Sirlin, C; Pfeffer, M. J. Organomet. Chem. 2003, 687, 313.
52. Eroshchenko, S. V.; Sinegovskaya, L. M.; Tarasova, O. A.; Frolov, Y. L.; Trofimov, B. A.; Ignatyev, I. S. Spectrochim. Acta, Part A 1990, 46A, 1505.
53. Previous work in this area has focused on the base-mediated cyclisations of the products from lithio-methoxyallene additions to carbonyls. These have been shown to cyclise to generate furan species; see: Reissig, H.-U.; Hormuth, S.; Schade, W.; Amombo, M. O.; Toshiko, W.; Pulz, R.; Hausherr, A.; Zimmer, R. J. Heterocycl. Chem. 2000, 37, 597, and references therein. It was our suspicion that the same type of transformation to form pyran ring systems may occur from allene alcohols derived from epoxide ring opening.
54. This was in contrast, however, to a literature publication which reported formation of furans: Hoff, S.; Brandsma, L.; Arens, J. F. Recl. Trav. Chim. PaysBas 1969, 88, 609.
55. Wattanasereekul, S.; Maier, M. E. Adv. Synth. Catal. 2004, 346, 855.
56. Denmark, S. E.; Fujimori, S. Org. Lett. 2002, 4, 3477.