A Combinatorial Synthesis of a Macrosphelide Library Utilizing a Palladium-Catalyzed Carbonylation on a Polymer Support

Angewandte Chemie - International Edition

Volumn 42, Issue 42, 2003, Pages 5230-5234

  Takahashi, Takashi ^a   Kusaka, Shin Ichi ^a   Doi, Takayuki ^a   Sunazuka, Toshiaki ^b   Omura, Satoshi ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

Chemoselectivity; Combinatorial chemistry; Macrosphelides; Palladium; Solid phase synthesis

Indexed keywords

CARBONYLATION; CATALYSIS; PALLADIUM; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVE CARBONYLATION; POLYMER SUPPORTS;

POLYMERS;

MACROSPHELIDE A; MACROSPHELIDE C; MACROSPHELIDE E; MACROSPHELIDE F; NATURAL PRODUCT; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHELATION; CHEMICAL MODIFICATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; STRUCTURE ACTIVITY RELATION;

EID: 0242636003     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352229     Document Type: Article

References (46)

1. J. Nielsen, Curr Opin. Chem. Biol. 2002, 6, 297-305.
2. L. A. Wessjohann, Curr. Opin. Chem. Biol. 2000, 4, 303-309.
3. K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739.
4. K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755; Angew. Chem. Int. Ed. 2000, 39, 734-739.
5. K. C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, N. P. King, M. R. V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. 1997, 109, 2181-2187; Angew. Chem. Int. Ed. Engl. 1997, 36, 2097-2103.
6. K. C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, N. P. King, M. R. V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. 1997, 109, 2181-2187; Angew. Chem. Int. Ed. Engl. 1997, 36, 2097-2103.
7. I. Hijikuro, T. Doi, T. Takahashi, J. Am. Chem. Soc. 2001, 123, 3716-3722.
8. a) M. Hayashi, Y.-P. Kim, H. Hiraoka, M. Natori, S. Takamatsu, T. Kawakubo, R. Masuma, K. Komiyama, S. Omura, J. Antibiot. 1995, 48, 1435-1439;
9. b) S. Takamatsu, Y.-P. Kim, M. Hayashi, H. Hiraoka, M. Natori, K. Komiyama, S. Omura, J. Antibiot. 1996, 49, 95-98.
10. a) T. A. Springer, Nature 1990, 346, 425-434;
11. b) E. C. Butcher, Cell 1991, 67, 1033-1036;
12. c) A. Fukami, K. Iijima, M. Hayashi, K. Komiyama, S. Omura, Biochem. Biophys. Res. Commun. 2002, 291, 1065-1070.
13. T. Sunazuka, T. Hirose, Y. Harigaya, S. Takamatsu, M. Hayashi, K. Komiyama, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1997, 119, 10247-10248.
14. a) Y. Kobayashi, B. G. Kumar, T. Kurachi, Tetrahedron Lett. 2000, 41, 1559-1563;
15. b) Y. Kobayashi, G. B. Kumar, T. Kurachi, H. P. Acharya, T. Yamazaki, T. Kitazume, J. Org. Chem. 2001, 66, 2011-2018;
16. c) Y. Kobayashi, H. P. Acharya, Tetrahedron Lett. 2001, 42, 2817-2820;
17. d) Y. Kobayashi, Y.-G. Wang, Tetrahedron Lett. 2002, 43, 4381-4384.
18. a) M. Ono, H. Nakamura, F. Konno, H. Akita, Tetrahedron: Asymmetry 2000, 11, 2753-2764;
19. b) H. Nakamura, M. Ono, Y. Shiba, H. Akita, Tetrahedron: Asymmetry 2002, 13, 705-713;
20. c) H. Nakamura, M. Ono, M. Makino, H. Akita, Heterocycles 2002, 57, 327-336.
21. G. V. M. Sharma, C. C. Mouli, Tetrahedron Lett. 2002, 43, 9159-9161.
22. R. Anacardio, A. Arcadi, G. D'Anniballe, F. Marinelli, Synthesis 1995, 831-836.
23. a) T. Takahashi, T. Nagashima, J. Tsuji, Chem. Lett. 1980, 369-372;
24. b) T. Takahashi, H. Ikeda, J. Tsuji, Tetrahedron Lett. 1980, 21, 3885-3888.
25. a) D. A. Evans, B. D. Allison, M. G. Yang, C. E. Masse, J. Am. Chem. Soc. 2001, 123, 10840-10852;
26. b) D. A. Evans, B. D. Allison, M. G. Yang, Tetrahedron Lett. 1999, 40, 4457-4460;
27. c) D. A. Evans, D. P. Halstead, B. D. Allison, Tetrahedron Lett. 1999, 40, 4461-4462.
28. 1H NMR compared with those reported in the literature. G. Guanti, L. Banfi, E. Narisano, Gazz. Chim. Ital. 1987, 117, 681.
29. a) H. X. Zhang, F. Guibe, G. Balavoine, J. Org. Chem. 1990, 55, 1857-1867;
30. b) N. D. Smith, J. Mancuso, M. Lautens, Chem. Rev. 2000, 100, 3257-3282.
31. J. A. Ellman, L. A. Tompson, Tetrahedron Lett. 1994, 35, 9333-9336.
32. 2O, MeOH, THF; HCl; CSA = camphorsulfonic acid).
33. a) T. Takahashi, H. Inoue, S. Tomita, T. Doi, A. M. Bray, Tetrahedron Lett. 1999, 40, 7843-7846;
34. b) T. Takahashi, H. Inoue, Y. Yamamura, T. Doi, Angew. Chem. 2001, 113, 3330-3333; T. Takahashi, H. Inoue, Y. Yamamura, T. Doi, Angew. Chem. 2001, 113, 3330-3333; Angew. Chem. Int. Ed. 2001, 40, 3230-3233;
35. b) T. Takahashi, H. Inoue, Y. Yamamura, T. Doi, Angew. Chem. 2001, 113, 3330-3333; T. Takahashi, H. Inoue, Y. Yamamura, T. Doi, Angew. Chem. 2001, 113, 3330-3333; Angew. Chem. Int. Ed. 2001, 40, 3230-3233;
36. b) T. Takahashi, H. Inoue, Y. Yamamura, T. Doi, Angew. Chem. 2001, 113, 3330-3333; T. Takahashi, H. Inoue, Y. Yamamura, T. Doi, Angew. Chem. 2001, 113, 3330-3333; Angew. Chem. Int. Ed. 2001, 40, 3230-3233;
37. c) M. Hashimoto, A. Mori, H. Inoue, H. Nagamiya, T. Doi, T. Takahashi, Tetrahedron Lett. 2003, 44, 1251-1254.
38. 2] as a catalyst. A. Cowell, J. K. Stille, Tetrahedron Lett. 1979, 20, 133-136.
39. 4 as a ligand.
40. 3, 16 was cleaved from the resin. K. Horita, T. Yoshioka, T. Tanaka, Y. Oikawa, O. Yonemitsu, Tetrahedron 1986, 42, 3021-3028.
41. -1 loading). Under the cyclization conditions, elimination of the β-acyloxy ester moiety was not observed.
42. The spectral data are given in the Supporting Information.
43. K. C. Nicolaou, X.-Y. Xiao, Z. Parandoosh, A. Senyei, M. P. Nova, Angew. Chem. 1995, 107, 2476-2479; Angew. Chem. Int. Ed. Engl. 1995, 34, 2289-2291.
44. K. C. Nicolaou, X.-Y. Xiao, Z. Parandoosh, A. Senyei, M. P. Nova, Angew. Chem. 1995, 107, 2476-2479; Angew. Chem. Int. Ed. Engl. 1995, 34, 2289-2291.
45. 1H NMR spectra. The acetal of the ethylene glycol moiety in C3 and C7 was intact under the cleavage conditions.
46. No other isomer was detected in LC/MS. However, as a referee pointed out, there is some uncertainty about the structure of the new lactones by the possibility of complete transesterification under acid cleavage conditions.