The manufacture of a homochiral 4-silyloxycyclopentenone intermediate for the synthesis of prostaglandin analogues

Organic Process Research and Development

Volumn 16, Issue 12, 2012, Pages 1905-1916

  Henschke, Julian P ^a   Liu, Yuanlian ^b   Huang, Xiaohong ^b   Chen, Yungfa ^a   Meng, Dechao ^b   Xia, Lizhen ^b   Wei, Xiuqiong ^b   Xie, Aiping ^b   Li, Danhong ^b   Huang, Qiang ^b   Sun, Ting ^b   Wang, Juan ^b   Gu, Xuebin ^b   Huang, Xinyan ^b   Wang, Longhu ^a   Xiao, Jun ^b   Qiu, Shenhai ^b  

^a ScinoPharm Taiwan Ltd   (Taiwan)

^b ScinoPharm (Changshu) Pharmaceutical Ltd   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE SALTS; CYCLOPENTENONES; ENZYMATIC RESOLUTIONS; HOMOCHIRAL; SITU RECYCLING; WITTIG REACTION;

ALDEHYDES; CHEMICAL REACTIONS; OLEFINS;

LIPIDS;

EID: 84871601208     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op300188x     Document Type: Article

References (41)

1. Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533
2. Stjernschantz, J.; Resul, B. Drugs Future 1992, 17, 691
3. Resul, B.; Stjernschantz, J.; No, K.; Liljebris, C.; Selen, G.; Astin, M.; Karlsson, M.; Bito, L. Z. J. Med. Chem. 1993, 36, 243
4. Sorbera, L. A.; Leeson, P. A.; Rabasseda, X.; Castaner, J. Drugs Future 2001, 26, 433
5. Yolin, S.; Walt, J. G.; Earl, M. Dermatol. Surg. 2010, 36, 638
6. Cohen, J. L. Dermatol. Surg. 2010, 36, 1361
7. Sorbera, L. A.; Castaner, J. Drugs Future 2000, 25, 41
8. Wang, Y.; Bolos, J.; Serradell, N. Drugs Future 2006, 31, 788
9. Sobera, L. A.; Castaner, J.; Mealy, N. E. Drugs Future 2004, 29, 336
10. Obadalová, I.; Pilarčík, T.; Slavíková , M.; Hájíček, J. Chirality 2005, 17, S109
11. Henschke, J. P.; Liu, Y. L.; Chen, Y. F.; Meng, D. C.; Sun, T. U.S. Patent 7,897,795, 2011.
12. Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969, 91, 5675
13. Sih, C. J.; Price, P.; Sood, R.; Salomon, R. G.; Peruzzotti, G.; Casey, M. J. Am. Chem. Soc. 1972, 94, 3643
14. Kluge, A. F.; Untch, K. G.; Fried, J. H. J. Am. Chem. Soc. 1972, 94, 7827
15. Pappo, R.; Collins, P. W. Tetrahedron Lett. 1972, 2627
16. Noyori, R.; Suzuki, M. Angew. Chem., Int. Ed. Engl. 1984, 23, 847
17. Suzuki, M.; Yanagisawa, A.; Noyori, R. J. Am. Chem. Soc. 1985, 107, 3348
18. Das, S.; Chandrasekhar, S.; Yadav, J. S.; Grée, R. Chem. Rev. 2007, 107, 3286
19. Gruber, L.; Tömösközi, I.; Major, E.; Kovács, G. Tetrahedron Lett. 1974, 3729
20. Collins, P. W; Dajani, E. Z.; Driskill, D. R.; Bruhn, M. S.; Jung, C. J; Pappo, R. J. Med. Chem. 1977, 20, 1152
21. Novák, L.; Szántay, Cs.; Meisel, T.; Aszódi, J.; Szabó, é.; Fekete, J. Tetrahedron 1985, 41, 435
22. Piancatelli, G. Heterocycles 1982, 19, 1735
23. Piancatelli, G.; D'Auria, M.; D'Onofrio, F. Synthesis 1994, 867
24. Babiak, K. A.; Ng, J. S.; Dygos, J. H.; Weyker, C. L.; Wang, Y.-F.; Wong, C.-H. J. Org. Chem. 1990, 55, 3377
25. Wong, C.-H.; Wang, Y.-F.; Hennen, W. J.; Babiak, K. A.; Dygos, J. H.; Ng, J. S. U.S. Patent 5,106,750, 1992.
26. Facile, autocatalytic decomposition (contact with only 0.2 equiv of ylide caused full decomposition) of the 4-silyloxy substituent via deprotonation α- to the aldehyde was proposed to be responsible for its base sensitivity. By contrast, when the 4-silyloxy substituent is absent, successful Wittig reaction with the identical ylide is possible (see Armstead, D. A.; Mann, J. Synth. Commun. 1985, 15, 1147)
27. See Ahrgren, L.; Sutin, L. Org. Process Res. Dev. 1997, 1, 425 for a description of a Sharpless asymmetric dihydroxylation on an industrial scale
28. 2PHAL provided a significant and useful rate acceleration; see Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am, Chem. Soc. 1988, 110, 1968
29. Although we had ready access to this ligand and with it only being used at 0.4 mol%, cheaper ligands and modified reaction conditions may provide similar results (see Eames, J.; Mitchell, H. J.; Nelson, A.; O'Brien, P.; Warren, S.; Wyatt, P. J. Chem. Soc., Perkin Trans. 1 1999, 1095 and references therein)
30. The addition of metalated derivatives of 1-bromo-2,2-dimethoxyethane to furfural, in an analogous fashion to that report Collins, P. W.; Kramer, S. W.; Gullikson, G. W. J. Med. Chem. 1987, 30, 1952 for a homologue of aldehyde 4 has shown promise.
31. Boulton, L. T.; Brick, D.; Fox, M. E.; Jackson, M.; Lennon, I. C.; McCague, R.; Parkin, N.; Rhodes, D.; Ruecroft, G. Org. Process Res. Dev. 2002, 6, 138
32. Reitz, A. B.; Nortey, S. O.; Jordan, A. D., Jr.; Mutter, M. S.; Maryanoff, B. E. J. Org. Chem. 1986, 51, 3302
33. Berndt, M.; Hölemann, A.; Niermann, A.; Bentz, C.; Zimmer, R.; Reissig, H. -U. Eur. J. Org. Chem. 2012, 1299
34. Dygos, J. H.; Adamek, J. P.; Babiak, K. A.; Behling, J. R.; Medich, J. R.; Ng, J. S.; Wieczorek, J. J. J. Org. Chem. 1991, 56, 2549
35. Piancatelli, G.; Scettri, A.; David, G.; D'Auria, M. Tetrahedron 1978, 34, 2775
36. Rodríguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. -J. Eur. J. Org. Chem. 1999, 2655
37. Rodríguez, A. R.; Spur, B. W. Tetrahedron Lett. 2003, 44, 7411
38. From a toxicological and environmental standpoint, 1,4-dioxane is an undesirable solvent; see Laird, T. Org. Process Res. Dev. 2012, 16, 1
39. Its impact was reduced by its use at only moderate volume/weight ratios (∼5-7 v/w) with an approximately equal portion of water. No 1,4-dioxane was detected in the target compounds by headspace GC analysis. Although the Piancatelli rearrangement has been reported to proceed in aq acetone, it was reported(32) to provide "poor yields" and "extremely low rate" when the substituent α- to the hydroxyl group was non-aromatic. Unfortunately solubility proved to be a constraint when using a completely aqueous system; see D'Auria, M. Heterocycles 2000, 52, 185 for the rearrangement.
40. In related prostaglandin analogue syntheses using similar conditions, yields of 40-72% for the sequential rearrangement and isomerisation have been reported; see Clissold, D. W.; Craig, S. W.; Gadikota, R. R.; He, M.; Jurayj, J. F.; Kazerani, S.; Rannala, E.; Sharma, P. K. U.S. Patent 7,109,371, 2006, (and refs 31 and 33 herein). Addition of 0.1-110 mol% hydroquinone, conducting the reaction in the dark or under an inert atmosphere have so far proven unhelpful. A future solvent screen to eliminate the use of dioxane altogether, or to minimise its volume further, should focus on water-miscible ethers or alcohols (transesterification needs to be taken into account), and a reinvestigation of the use of acetone is required.
41. Henschke, J. P.; Liu, Y. L.; Xia, L. Z.; Chen, Y. F. PCT Int. Appl. Pub. WO/2012/048447 A1, 2012.