Enzyme- and ruthenium-catalyzed dynamic kinetic asymmetric transformation of 1,5-diols. Application to the synthesis of (+)-Solenopsin A

Journal of Organic Chemistry

Volumn 74, Issue 5, 2009, Pages 1988-1993

  Leijondahl, Karin ^a   Borén, Linnéa ^a   Braun, Roland ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREO SELECTIVITIES; DYNAMIC KINETIC ASYMMETRIC TRANSFORMATIONS; NATURAL PRODUCT SYNTHESIS; RUTHENIUM CATALYSIS;

RUTHENIUM;

ACETOACETIC ACID; RUTHENIUM; SOLENOPSIN A; TRIACYLGLYCEROL LIPASE;

ARTICLE; ASYMMETRIC CATALYSIS; DYNAMIC KINETIC ASYMMETRIC TRANSFORMATION; ENANTIOMER; ENZYME MECHANISM; ENZYME SYNTHESIS; KINETICS; RACEMIZATION; STEREOCHEMISTRY;

ALCOHOLS; ALKALOIDS; CATALYSIS; KINETICS; LIPASE; MOLECULAR STRUCTURE; RUTHENIUM; STEREOISOMERISM;

EID: 64249157719     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8025109     Document Type: Article

References (44)

1. (a) Stürmer, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1173.
2. (b) Larsson, A. L. E.; Persson, B. A.; Bäckvall, J.-E. Angew. Chem., Int. Ed. Engl. 1997, 36, 1211.
3. (a) Choi, J. H.; Choi, Y. K.; Kim, Y. H.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972-1977.
4. (b) Martín-Matute, B.; Edin, M.; Bogàr, K.; Kaynak, F. B.; Bäckvall, J.-E. J. Am. Chem. Soc. 2005, 127, 8817-8825.
5. (c) Kim, N.; Ko, S.-B.; Kwon, M. S.; Kim, M.-J.; Park, J. Org. Lett. 2005, 7, 4523-4526.
6. (a) Strübing, D.; Krumlinde, P.; Piera, J.; Bäckvall, J.-E. Adv. Synth. Catal. 2007, 349, 1577-1581.
7. See also: (b) Atuu, M. R.; Hossian, M. M. Tetrahedron Lett. 2007, 48, 3875.
8. Paetzold, J.; Bäckvall, J.-E. J. Am. Chem. Soc. 2005, 127, 17620-17621.
9. (a) Parvulescu, A. N.; Jacobs, P. A.; De Vos, D. E. Chem. Eur. J. 2007, 13, 2034-2043.
10. (b) Kim, M. J.; Kim, W. H.; Han, K.; Choi, Y. K.; Park, J. Org. Lett. 2007, 9, 1157-1159.
11. Steinreiber, J.; Faber, K.; Griengl, H. Chem. Eur. J. 2008, 14, 8060-8072.
12. (a) Fransson, A.-B.; Xu, Y.; Leijondahl, K.; Bäckvall, J.-E. J. Org. Chem. 2006, 71, 6309-6316.
13. (b) Olofsson, B.; Bogár, K.; Fransson, A.-B.; Bäckvall, J.-E. J. Org. Chem. 2006, 71, 8256-8260.
14. (a) Edin, M.; Steinreiber, J.; Bäckvall, J.-E. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5761-5766.
15. (b) Martín- Matute, B.; Edin, M.; Bäckvall, J.-E. Chem. Eur. J. 2006, 12, 6053-6061.
16. Edin, M.; Martín- Matute, B.; Bäckvall, J.-E. Tetrahedron: Asymmetry 2006, 17, 708-715.
17. (a) Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. J. Org. Chem. 1996, 61, 7309-7315.
18. (b) Solladié, G.; Huser, N. Recl. Trav. Chim. Pays-Bas 1995, 114, 153-156.
19. Leijondahl, K.; Borén, L.; Braun, R.; Bäckvall, J.-E. Org. Lett. 2008, 10, 2027-2030.
20. For a mechanistic study of the second generation ruthenium catalyst see: Martín-Matute, B.; Åberg, J. B.; Edin, M.; Bäckvall, J.-E. Chem. Eur. J. 2007, 13, 6063-6072.
21. The use of two different enzymes in entry 1 of Table 1 (footnote d) is because CALB only reacts with the alcohol next to the methyl group and is essentially unreactive toward the alcohol next to the carboxy group. In this way, a selective acylation of the former alcohol group is obtained by using CALB in the beginning of the reaction (PS-C II gives a lower selectivity of that alcohol group). In the second step PS-C II is required since CALB stops after the first step.
22. (a) Sexton, A. R.; Britton, E. C. J. Am. Chem. Soc. 1953, 75, 43574358.
23. (b) Summerbell, R. K.; Jerina, D. M.; Grula, R. J. J. Org. Chem. 1962, 27, 4433-4436.
24. Träff, A.; Bogár, K.; Warner, M.; Bäckvall, J.-E. Org. Lett. 2008, 10, 4807-4810.
25. Hodgson, D. M.; Chung, Y. K.; Paris, J.-M. Synthesis 2005, 13, 22642266.
26. When a DKR was performed with catalyst 2, 82% conversion was obtained after 22 h, and the acetate showed an ee of 84%, indicating that the racemization has to be studied further.
27. Hoff, B. H.; Anthonsen, T. Tetrahedron: Asymmetry 1999, 10, 14011412.
28. The reaction was run on a 0.2 mmol scale in 1 mL of toluene under argon, and a sample was taken after 2 h. Analysis by chiral CG showed 94% de (i.e., anti:syn ) 97:3) of the product at 26% conversion. This corresponds to a pseudo E value of 44.
29. It is not clear why the DYKAT of diol 1i gives such a poor diastereoselectivity, but one reason may be that the first acylation occurs to some extent on the alcohol next to the chloro group. Sequential use of enzymes CALB and PS-C II (added after 5 h) was employed since CALB reacts slowly with the chlorohydrin alcohol but fast with the alcohol next to the methyl group. However, the fact that DYKAT of the monoacetate (2RS,6R)-9 gave only a diastereoselectivity of 89:11, in spite of the fact that the pseudo E value is 44 (and is expected to give a diastereoselectivity of 98:2 with an efficient epimerization), shows that there are other explanations. One obvious explanation is that the rate of epimerization is not fast enough. Another explanation is that some reversibility of the acylation reactions is occurring and this will lower the final isomeric purity of the product.
30. Leclercq, S.; Thirionet, I.; Broeders, F.; Daloze, D.; Vander Meer, R.; Braeckman, J. C. Tetrahedron 1994, 50, 8465-8478.
31. (a) Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477.
32. (b) Guilloteau-Bertin, B.; Compère, D.; Gil, L.; Marazano, C.; Das, B. C. Eur. J. Org. Chem. 2000, 1391-1399.
33. (c) Dobbs, A. P.; Guesné, S. J. J. Synlett 2005, 13, 2101-2103.
34. (d) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446.
35. For a review, see (e) Leclercq, S.; Daloze, D.; Braekman, J.-C. Org. Prep. Proced. Int. 1996, 28, 501-543.
36. Itoh, T.; Mitsukura, K.; Kanphai, W.; Takagi, Y.; Kihara, H.; Tsukube, H. J. Org. Chem. 1997, 62, 9165-9172.
37. Pettersson-Fasth, H.; Riesinger, S. W.; Bäckvall, J.-E. J. Org. Chem. 1995, 60, 6091-6096.
38. Bäckvall, J.-E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619-4631.
39. Bäckvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826-831.
40. Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596.
41. Pàmies, O.; Bäckvall, J.-E. Adv. Synth. Catal. 2001, 343, 726-731.
42. Girard, N.; Hurvois, J.-P. Synth. Commun. 2005, 35, 711-723.
43. Uenichi, J.; Ohmi, M.; Ueda. A. Tetrahedron Asymmetry 2005, 16, 1299-1303.
44. Kazlauskas, R. J.; Weissfloch. A. N. E.; Rappaport. A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665.