AAA in KAT/DYKAT processes: First- and second-generation asymmetric syntheses of (+)- and (-)-cyclophellitol

Chemistry - A European Journal

Volumn 7, Issue 17, 2001, Pages 3768-3775

  Trost, Barry M ^a   Patterson, Daniel E ^a   Hembre, Erik J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Allyl complexes; Asymmetric catalysis; Natural products; Palladium; Total synthesis

Indexed keywords

ENZYMES; ESTERS; STEREOCHEMISTRY;

KINETIC ASYMMETRIC TRANSFORMATIONS (KAT);

ALKYLATION;

4 TERT BUTYL DIMETHYLSILYLOXY 2,2 DIMETHYLBUTYRIC ACID; ALLYL COMPOUND; ANTI HIV AGENTS; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BETA GLUCOSIDASE; BUTYRIC ACID DERIVATIVE; CONDURITOL B; CYCLOHEXANOL DERIVATIVE; CYCLOHEXENE DERIVATIVE; CYCLOPHELLITOL; ENZYME INHIBITOR; ESTER DERIVATIVE; GLYCOSIDASE INHIBITOR; HYDROXYL GROUP; NATURAL PRODUCT; PALLADIUM; RHENIUM; UNCLASSIFIED DRUG;

AGARICALES; ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; DRUG SYNTHESIS; ENANTIOMER; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS; TECHNIQUE;

AGARICALES; ANTI-HIV AGENTS; BETA-GLUCOSIDASE; CATALYSIS; CYCLOHEXANOLS; ENZYME INHIBITORS; METHODS; RHENIUM; STEREOISOMERISM;

EID: 0035801528     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010903)7:17<3768::AID-CHEM3768>3.0.CO;2-C     Document Type: Article

References (65)

1. S. Atsumi, K. Umezawa, H. Iinuma, H. Naganawa, H. Nakamura, Y. Iitaka, T. Takeuchi, J. Antibiot. 1990, 43, 49.
2. S. Atsumi, H. Iinuma, C. Nosaka, K. Umezawa, J. Antibiot 1990, 43, 1579.
3. See also: Y. Nishimura, Stud. Nat. Prod. Chem. 1997, 19 (Structure and Chemistry, Part E), 351.
4. For a lead reference in glycosidase inhibitors, see: N. Asano, R. J. Nash, R. S. Molyneux, G. W. J. Fleet, Tetrahedron: Asymmetry 2000, 11, 1645.
5. For a recent paper on novel design of carbocyclic glycosidase inhibitors, see: K. S. E. Tanaka, G. C. Winters, R. J. Batchelor, F. W. B. Einstein, A. S. Bennet, J. Am. Chem. Soc. 2001, 123, 998.
6. a) T. Akiyama, H. Shima, M. Ohnari, T. Okazaki, S. Ozaki, Bull. Chem. Soc. Jpn. 1993, 66, 3760;
7. b) T. Akiyama, M. Ohnari, H. Shima, S. Ozaki, Syntlett 1991, 831-83;
8. c) T. K. M. Shing, V. W. F. Tai, J. Chem. Soc. Chem. Commun. 1993, 995;
9. d) T. K. M. Shing, V. W. F. Tai, J. Chem. Soc. Perkin Trans. 1 1994, 2017;
10. e) K. I. Sato, M. Bokura, H. Moriyama, T. Igarashi, Chem. Lett. 1994, 37;
11. f) K. Tatsuta, Y. Niwata, K. Umezawa, K. Toshima, M. Nakata, Carbohydrate Res. 1991, 222, 189;
12. g) K. Tatsuta, Y. Niwata, K. Umezawa, K. Toshima, M. Nakata, Tetrahedron Lett. 1990, 31, 1171;
13. h) K. Tatsuta, Y. Niwata, K. Umezawa, K. Toshima, M. Nakata, Tetrahedron Lett. 1990, 31, 1171;
14. i) P. Letelier, R. Ralainairina, B. Beaupere, R. Uzan, Synthesis 1997, 925;
15. j) M. E. Jung, S. W. T. Choe, J. Org. Chem. 1995, 60, 3280;
16. k) F. E. Ziegler, Y. Wang, J. Org. Chem. 1998, 63, 426;
17. F. E. Ziegler, Y. Wang, J. Org. Chem. 1998, 63, 7920;
18. l) R. E. McDevitt, B. Fraser-Reid, J. Org. Chem. 1994, 59, 3250;
19. m) H. Takahashi, T. Iimori, S. Ikegami, Tetrahedron Lett. 2000, 39, 6939.
20. R. H. Schlessinger, C. P. Bergstrom, J. Org. Chem. 1995, 60, 16.
21. For a preliminary report of a portion of this work, see: B. M. Trost, E. J. Membre, Tetrahedron Lett. 1999, 40, 219.
22. Z.-X. Guo, A. H. Haines, S. M. Pyke, S. G. Pyke, R. J. K. Taylor, Carbohydr. Res. 1994, 264, 147.
23. For reviews, see: M. Balci, Y. Sütbeyaz, H. Secen, Tetrahedron 1990, 46, 3715;
24. T. Suami, S. Ogawa, Adv. Carbohydr. Chem. Biochem. 1990, 48, 21;
25. J. J. Kiddle, Chem. Rev. 1995, 95, 2189.
26. For a few recent examples, see: O. Arjona, A. de Dios, J. Plument, B. Saez, Tetrahedron Lett. 1995, 36, 1319;
27. J. E. Innes, P. J. Edwards, S. V. Ley, J. Chem. Soc. Perkin Trans. 1 1997, 795;
28. C. Sanfilippo, A. Patti, G. Nicolosi, Tetrahedron: Asymmetry 1999, 10, 3273;
29. M. Honzumi, K. Hiroya, T. Taniguchi, K. Ogasawara, Chem. Commun. 1999, 1985;
30. O. Plettenburg, S. Adelt, G. Vogel, H. J. Altenbach, Tetrahedron: Asymmetry 2000, 11, 1057;
31. K. Sato, S. Sakuma, S. Muramatsu, M. Bokura, Chem. Lett. 1991, 147;
32. N. Chida, M. Ohtsuka, K. Nakazawa, S. Ogawa, J. Org. Chem. 1991, 56, 2976;
33. T. K. Park, S. J. Danishefsky, Tetrahedron Lett. 1994, 35, 2667;
34. S. Amano, N. Ogawa, M. Ohtsuda, N. Chida, Tetrahedron 1999, 55, 2205.
35. B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395;
36. B. M. Trost, C.-B. Lee, in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000, Chapter 8E, pp. 593-650.
37. B. M. Trost, D. E. Patterson, E. J. Hembre, J. Am. Chem. Soc. 1999, 121, 10834.
38. B. M. Trost, Acc. Chem. Res. 1996, 29, 355.
39. W. C. Still, A. Mitra, J. Am. Chem. Soc. 1978, 100, 1927.
40. For the synthesis of (phenylsulfonyl)nitromethane see, P. A. Wade, H. R. Hinney, N. V. Amin, P. D. Vail, S. D. Morrow, S. A. Hardinger, M. S. Saft, J. Org. Chem. 1981, 46, 765.
41. a) B. M. Trost, R. Madsen, S. D. Guile, B. Brown, J. Am. Chem. Soc. 2000, 122, 5947;
42. b) B. M. Trost, D. Stenkamp, S. R. Pulley, Chem. Eur. J. 1995, 1, 568;
43. c) B. M. Trost, R. Madsen, S. G. Guile, A. E. H. Elia, Angew. Chem. 1996, 108, 1666;
44. Angew. Chem. Int. Ed. Engl. 1996, 55, 1569;
45. d) B. M. Trost, R. Madsen, S. G. Guile, Tetrahedron Lett. 1997, 38, 1707.
46. B. M. Trost, R. Brauslau, J. Org. Chem. 1988, 55, 532.
47. P. Ceccherelli, M. Curini, M. C. Marcotullio, F. Epifano, O. Rosati, Synth. Commun. 1998, 28, 3057.
48. G. A. Olah, B. G. B. Gupta, Synthesis 1980, 44.
49. J. E. McMurry, J. Melton, J. Org. Chem. 1973, 38, 4367.
50. W. Adam, M. Makosza, C. R. Saha-Moller, C. G. Zhao, Synlett 1998, 1335.
51. a) W. H. Rastetter, T. J. Richard, M. D. Lewis, J. Org. Chem. 1978, 43, 3163;
52. b) P. A. Bartlett, L. A. McQuaid, J. Am. Chem. Soc. 1984, 106, 7854.
53. a) K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95, 6136;
54. b) M. Bailey, I. Staton, P. R. Ashton, I. E. Marko, W. D. Ollis, Tetrahedron: Asymmetry 1991, 2, 495.
55. For reviews on the MTOR-catalyzed epoxidation, see a) W. A. Herrmann, R. M. Kratzer, H. Ding, W. R. Theil, H. Glas, J. Organomet. Chem. 1998, 555, 293;
56. b) A. Gansäuer, Angew. Chem. 1997, 109, 2701;
57. Angew. Chem. Int. Ed. Engl. 1997, 36, 2591.
58. W. Adam, C. M. Mitchell, Angew. Chem. 1996, 108, 578;
59. Angew. Chem. Int. Ed. Engl. 1996, 35, 533.
60. a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189;
61. b) C. Coperet, H. Adolfson, K. B. Sharpless, Chem. Commun. 1997, 1566;
62. c) M. L. A. van Vliet, I. W. C. E. Arends, R. A. Sheldon, Chem. Commun. 1999, 821;
63. d) H. Adolfsson, A. Converso, K. B. Sharpless, Tetrahedron Lett. 1999, 41, 3991.
64. For the case of an allyl alcohol, see: T. R. Boehlow, C. D. Spilling, Tetrahedron Lett. 1996, 37, 2717.
65. B. M. Trost, J. Dudash, Jr, E. J. Hembre, Chem. Eur. J. 2001, 7, 1619.