Stereoselective synthesis of the hydrophobic side chain of scyphostatin

Australian Journal of Chemistry

Volumn 57, Issue 5, 2004, Pages 439-447

  Takagi, Ryukichi ^a   Tsuyumine, Shinjiro ^a   Nishitani, Hiroko ^a   Miyanaga, Wataru ^a   Ohkata, Katsuo ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; CATALYSIS; ENZYME KINETICS; HALOGENATION; HYDROPHOBICITY; LITHIUM COMPOUNDS; OLEFINS; OPTICAL ROTATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

NATURAL PRODUCTS; NEGISHI COUPLING REACTION; OLEFINATION; SYNTHETIC PATHWAYS;

DRUG PRODUCTS;

EID: 2542593880     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH03298     Document Type: Article

References (42)

1. (a) M. Tanaka, F. Nara, K. Suzuki-Konagai, T. Hosoya, T. Ogita, J. Am. Chem. Soc. 1997, 119, 7871. doi:10.1021/JA9713385
2. (b) F. Nara, M. Tanaka, T. Hosoya, K. Suzuki-Konagai, T. Ogita, J. Antibiot. 1999, 52, 525.
3. (c) F. Nara, M. Tanaka, S. Masuda-Inoue, Y. Yamamoto, H. Doi-Yoshioka, K. Suzuki-Konagai, S. Kumakura, T. Ogita, J. Antibiot. 1999, 52, 531.
4. (a) R. Takagi, A. Sasaoka, H. Nishitani, S. Kojima, Y. Hiraga, K. Ohkata, J. Chem. Soc., Perkin Trans. 1 1998, 925. doi:10.1039/A707204J
5. (b) H. Nishitani, A. Sasaoka, M. Tokumasu, K. Ohkata, Heterocycles 1999, 50, 35.
6. (c) M. Tokumasu, H. Ando, Y. Hiraga, S. Kojima, K. Ohkata, J. Chem. Soc., Perkin Trans. 11999, 489. doi:10.1039/A808526I
7. (d) Y. Hiraga, M. Ago, M. Tokumasu, K. Kaku, K. Ohkata, Aust. J. Chem. 2000, 55, 909. doi:10.1071/CH00101
8. (e) N. Ohmori, J. Chem. Soc., Perkin Trans. 1 2002, 755. doi:10.1039/B110607B
9. (a) R. Takagi, W. Miyanaga, Y. Tamura, K. Ohkata, Chem. Commun. 2002, 2096. doi:10.1039/B206163E
10. (b) R. Takagi, W. Miyanaga, Y. Tamura, S. Kojima, K. Ohkata, Heterocycles 2003, 60, 785.
11. (a) M. K. Gurjar, S. Hotha, Heterocycles 2000, 53, 1885.
12. (b) T. Katoh, T. Izuhara, Tetrahedron Lett. 2000, 41, 7651. doi:10.1016/S0040-4039(99)02005-5
13. (c) T. Izuhara, T. Katoh, Org. Lett. 2001, 3, 1653. doi:10.1021/ OL015873S
14. (d) K. A. Runcie, R. J. K. Taylor, Org. Lett. 2001, 3, 3237. doi:10.1021/OL0164132
15. (e) H. Fujioka, N. Kotoku, Y. Sawama, Y. Nagatomi, Y. Kita, Tetrahedron Lett. 2002, 43, 4825. doi: 10.1016/80040-4039(02) 00916-4
16. (f) L. M. Murray, P. O'Brien, R. J. K. Taylor, Org. Lett. 2003, 5, 1943. doi:10.1021/OL034521D
17. (g) E. Martin, M.-M. Cäcilia, E. M. Martin, Tetrahedron 2003, 59, 7949. doi:10.1016/S0040-4020(03)00981-5
18. (h) T. R. Hoye, M. A. Tennakoon, Org. Lett. 2000, 2, 1481. doi:10.1021/OL0058386
19. M. Inoue, W. Yokota, M. G. Murugeshm, T. Izuhara, T. Katoh, 45th Symposium on the Chemistry of Natural Products, Oct. 6-8, 2003, pp. 49-54, Kyoto.
20. S. Saito, N. Tanaka, K. Fujimoto, H. Kogen, Org. Lett. 2000, 2, 505. doi:10.1021/OL991351P
21. Preliminary presentation of our initial route: H. Nishitani, S. Takenami, R. Takagi, K. Ohkata, Chemical Society of Japan Annual Meeting, Mar. 28-31, 2000, 3PB027, Chiba.
22. (a) G. M. R. Tombo, H.-P. Schär, X. F. Busquets, O. Ghisalba, Tetrahedron Lett. 1986, 27, 5707. doi:10.1016/S0040-4039(00) 85306-X
23. (b) J. C. Anderson, S. V. Ley, S. P. Marsden, Tetrahedron Lett. 1994, 35, 2087. doi:10.1016/S0040-4039(00)73057-7
24. The enantioselectivity in the PPL-catalyzed asymmetric acetylation was determined by converting the alcohol 7 into its benzoate, followed by analysis with a DAICEL CHIRALCEL-OD column (hexane/AcOEt, 400:1). (The racemate of 18 was used as a control.)
25. The geometric isomers were separated with preparative TLC. The geometries of the isomers were determined by dif-NOE. When the H13′ vinyl proton of the Z-isomer was irradiated, the intensity of the H11′ methylene proton signal was enhanced by 9.1%.
26. The diasteromer mixture of Z-11 was converted into a diasteromeric mixture of the ethyl ester 31 via six steps (34%: hydride reduction of the ester, mesylation of the alcohol, hydride reduction of the mesylate, cleavage of the TBS ether, oxidation, and HWE using 5).
27. M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, T. Sakai, Tetrahedron Lett. 1984, 25, 2183. doi:10.1016/S0040-4039(01) 80205-7
28. (a) E. Negishi, L. F. Valente, M. Kobayashi, J. Am. Chem. Soc. 1980, 102, 3298.
29. (b) T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J. Am. Chem. Soc. 1984, 106, 158.
30. (a) T. Kitahara, H. Shimizu, J. Nat. Prod. 1998, 61, 551. doi:10.1021/NP970480G
31. (b) M. G. Organ, Y. V Bilokin, S. Bratovanov, J. Org. Chem. 2002, 67, 5176. doi:10.1021/JO0201777
32. E. J. Corey, P. L. Fuchs, Tetrahedron Lett. 1972, 13, 3769. doi:10.1016/S0040-4039(01)94157-7
33. I. Fleming, T. W. Newton, F. Roessler, J. Chem. Soc., Perkin Trans. 1 1981, 2527.
34. D. P. Stamos, A. G. Taylor, Y. Kishi, Tetrahedron Lett. 1996, 37, 8647. doi:10.1016/S0040-4039(96)02000-X
35. A. B. Smith, III, T. J. Beauchamp, M. J. LaMarche, M. D. Kaufman, Y. Qiu, H. Arimoto, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8654. doi:10.1021/JA0015287
36. (a) H. de Koning, G. N. Mallo, A. Springer-Fidder, K. E. C. Subramanian-Erhart, H. O. Huisman, Recueil 1973, 92, 683.
37. (b) H. de Koning, K. E. C. Subramanian-Erhart, H. O. Huisman, Synth. Commun. 1973, 3, 25.
38. P. F. Wiley, K. Gerzon, E. H. Flynn, M. V. Sigal, O. Weaver, U. C. Quarck, R. R. Chauvette, R. Monahan, J. Am. Chem. Soc. 1957, 79, 6062.
39. J. Hao, J. Aiguade, C. J. Forsyth, Tetrahedron Lett. 2001, 42, 821. doi: 10.1016/80040-4039(00)02157-2
40. I. Shin, H.-Q. Zhou, N. L. S. Que, H.-W. Liu, J. Org. Chem. 1993, 58, 2923.
41. N. Murakami, M. Sugimoto, T. Nakajima, M. Kawanishi, Y. Tsutsui, M. Kobayashi, Bioorg. Med. Chem. 2000, 8, 2651. doi:10.1016/S0968-0896(00)00199-1
42. T. Oka, A. Murai, Tetrahedron 1998, 54, 1. doi:10.1016/80040-4020(97) 10253-8