A direct catalytic asymmetric aldol reaction of α-sulfanyl lactones: Efficient synthesis of SPT inhibitors

Angewandte Chemie - International Edition

Volumn 51, Issue 17, 2012, Pages 4218-4222

  Takechi, Sho ^a,b   Yasuda, Shigeo ^a   Kumagai, Naoya ^a   Shibasaki, Masakatsu ^a  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

aldol reaction; asymmetric catalysis; silver; SPT inhibitor; sulfanyl lactone

Indexed keywords

ALDOL REACTIONS; ASYMMETRIC ALDOL REACTIONS; ASYMMETRIC CATALYSIS; EFFICIENT SYNTHESIS; ENANTIOSELECTIVE; FUNCTIONALIZED; HYDROXY GROUPS; SPT INHIBITOR; SULFANYL LACTONE; TERTIARY ALCOHOLS;

CATALYSIS; SILVER;

CONDENSATION REACTIONS;

ALDEHYDE; ENZYME INHIBITOR; LACTONE; SERINE PALMITOYLTRANSFERASE; SULFUR DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; ENZYME INHIBITORS; LACTONES; MOLECULAR STRUCTURE; SERINE C-PALMITOYLTRANSFERASE; STEREOISOMERISM; SULFUR COMPOUNDS;

EID: 84859970264     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201200520     Document Type: Article

References (51)

1. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580
2. Modern Aldol Reactions (Ed.:, R. Mahrwald,), Wiley-VCH, Berlin, 2004
3. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471
4. B. M. Trost, C. S. Brindle, Chem. Soc. Rev. 2010, 39, 1600.
5. Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942
6. Angew. Chem. Int. Ed. Engl. 1997, 36, 1871
7. N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 4168
8. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395
9. B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003
10. R. Mahrwald, B. Ziemer, Tetrahedron Lett. 2002, 43, 4459.
11. Y. Suto, R. Tsuji, M. Kanai, M. Shibasaki, Org. Lett. 2005, 7, 3757; for the use of activated amides, see
12. S. Saito, S. Kobayashi, J. Am. Chem. Soc. 2006, 128, 8704; for β,γ-unsaturated esters, see
13. A. Yamaguchi, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 10842; for thioamides, see
14. M. Iwata, R. Yazaki, Y. Suzuki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 18244
15. M. Iwata, R. Yazaki, I.-H. Chen, D. Sureshkumar, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2011, 133, 5554; for 5H-oxazol-4-ones, see
16. T. Misaki, G. Takimoto, T. Sugimura, J. Am. Chem. Soc. 2010, 132, 6286; for an example of a direct catalytic asymmetric aldol reaction of thiazolidinethiones where the use of a stoichiometric amount of silylating reagent was essential, see
17. D. A. Evans, C. W. Downey, J. L. Hubbs, J. Am. Chem. Soc. 2003, 125, 8706.
18. There are numerous examples of direct aldol reactions using aldol donors bearing electron-withdrawing α substituents that readily undergo enolization under mild basic conditions. For pioneering work in this area that uses α-isocyanoacetates, see:, Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405.
19. N. Umebayashi, Y. Hamashima, D. Hashizume, M. Sodeoka, Angew. Chem. 2008, 120, 4264
20. Angew. Chem. Int. Ed. 2008, 47, 4196; for a selection of examples that use active methylene compounds as substrates and where the aldol reaction is coupled with a subsequent intramolecular reaction to suppress the retro-aldol reaction, see: for the use of α-isocyanoacetates, see
21. L. Li, E. G. Klauber, D. Seidel, J. Am. Chem. Soc. 2008, 130, 12248; for an example of a reaction between α-isothiocyanato acetates and ketones, see
22. T. Yoshino, H. Morimoto, G. Lu, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 17082; for an example where the direct catalytic asymmetric aldol reaction of α-cyanoesters is productive, see
23. R. Kuwano, H. Miyazaki, Y. Ito, Chem. Commun. 1998, 71.
24. N. D. Epiotis, R. L. Yates, F. Bernardi, S. Wolfe, J. Am. Chem. Soc. 1976, 98, 5435
25. J.-M. Lehn, G. Wipff, J. Am. Chem. Soc. 1976, 98, 7498
26. E. Schaumann, Top. Curr. Chem. 2007, 274, 1.
27. M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187
28. N. Kumagai, M. Shibasaki, Angew. Chem. 2011, 123, 4856
29. Angew. Chem. Int. Ed. 2011, 50, 4760; for Lewis acid/Lewis base, see
30. M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491
31. D. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth, T. Lectka, Acc. Chem. Res. 2008, 41, 655; for Lewis acid/Brønsted acid, and Lewis acid/Lewis acid, see
32. H. Yamamoto, K. Futatsugi, Angew. Chem. 2005, 117, 1958
33. Angew. Chem. Int. Ed. 2005, 44, 1924
34. H. Yamamoto, K. Futatsugi, in Acid Catalysis in Modern Organic Synthesis (Eds.:, H. Yamamoto, K. Ishihara,), Wiley-VCH, Weinheim, 2008.
35. R. Yazaki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 5522
36. R. Yazaki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 10275.
37. N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5360
38. M. Wadamoto, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 14556.
39. For an example of a catalytic asymmetric reaction with a silver complex using the chiral biaryl-type bisphosphine ligand (R)-DTBM-Segphos, in which it is believed that 1:1 (R)-DTBM-Segphos/AgHMDS complex is the active catalyst, see:, Y. Yamashita, T. Imaizumi, X.-X. Guo, S. Kobayashi, Chem. Asian J. 2011, 6, 2550.
40. G. H. Harris, E. T. T. Jones, M. S. Meinz, M. Nallin-Omstead, G. L. Helms, G. F. Bills, D. Zink, K. E. Wilson, Tetrahedron Lett. 1993, 34, 5235-5238.
41. T. Esumi, Y. Iwabuchi, H. Irie, S. Hatakeyama, Tetrahedron Lett. 1998, 39, 877
42. A. Pollex, L. Abraham, J. Müller, M. Hiersemann, Tetrahedron Lett. 2004, 45, 6915
43. K. Morokuma, K. Takahashi, J. Ishihara, S. Hatakeyama, Chem. Commun. 2005, 2265
44. A. Pollex, A. Millet, J. Müller, M. Hiersemann, L. Abraham, J. Org. Chem. 2005, 70, 5579
45. S. M. Goldup, C. J. Pilkington, A. J. P. White, A. Burton, A. G. M. Barrett, J. Org. Chem. 2006, 71, 6185
46. H.-S. Byun, X. Lu, R. Bittman, Synthesis 2006, 2447
47. A. K. Ghosh, J. Kass, Org. Lett. 2012, 14, 510.
48. M. Aoki, H. Kato, M. Sudoh, T. Tsukuda, M. Masubuchi, K. Kawasaki, PCT Int. Appl. WO2004/071503A1, 2004
49. M. Sudoh, T. Tsukuda, M. Masubuchi, K. Kawasaki, T. Murata, F. Watanabe, H. Fukuda, S. Komiyama, T. Hayase, PCT Int. Appl. WO2005/005372A1, 2005.
50. For NA255, see:, H. Sakamoto, K. Okamoto, M. Aoki, H. Kato, A. Katsume, A. Ohta, T. Tsukuda, N. Shimma, Y. Aoki, M. Arisawa, M. Kohara, M. Sudoh, Nat. Chem. Biol. 2005, 1, 333.
51. T. Umehara, M. Sudoh, F. Yasui, C. Matsuda, Y. Hayashi, K. Chayama, M. Kohara, Biochem. Biophys. Res. Commun. 2006, 346, 67, and references therein.