Asymmetric total syntheses of platensimycin

Angewandte Chemie - International Edition

Volumn 46, Issue 21, 2007, Pages 3942-3945

  Nicolaou, K C ^a,b   Edmonds, David J ^a,b   Li, Ang ^a,b   Tria, G Scott ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Antibiotics; Asymmetric synthesis; Drug resistance; Natural products; Total synthesis

Indexed keywords

ASYMMETRIC SYNTHESIS; DRUG RESISTANCE; NATURAL PRODUCTS; SPIROCYCLIC INTERMEDIATES; TOTAL SYNTHESIS;

ALKYLATION; CATALYST ACTIVITY; CHIRALITY; ISOMERIZATION;

ANTIBIOTICS;

ADAMANTANE; AMINOBENZOIC ACID DERIVATIVE; ANILIDE; PLATENSIMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ADAMANTANE; AMINOBENZOIC ACIDS; ANILIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 34250702223     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700586     Document Type: Article

References (39)

1. a) J. Wang, S. M. Soisson, K. Young, W. Shoop, S. Kodali, A. Galgoci, R. Painter, G. Parthasarathy, Y. S. Tang, R. Cummings, S. Ha, K. Dorso, M. Motyl, H. Jayasuriya, J. Ondeyka, K. Herath, C. Zhang, L. Hernandez, J. Allocco, A. Basilio, J. R. Tormo, O. Genilloud, F. Vicente, F. Pelaez, L. Colwell, S. H. Lee, B. Michael, T. Felcetto, C. Gill, L. L. Silver, J. D. Hermes, K. Bartizal, J. Barrett, D. Schmatz, J. W. Becker, D. Cully, S. B. Singh, Nature 2006, 441, 358-361;
2. b) S. B. Singh, H. Jayasuriya, J. G. Ondeyka, K. B. Herath, C. Zhang, D. L. Zink, N. N. Tsou, R. G. Ball, A. Basilio, O. Genilloud, M. T. Diez, F. Vicente, F. Pelaez, K. Young, J. Wang, J. Am. Chem. Soc. 2006, 128, 11916-11920.
3. K. C. Nicolaou, A. Li, D. J. Edmonds, Angew. Chem. 2006, 118, 7244-7248;
4. Angew. Chem. Int. Ed. 2006, 45, 7086-7090.
5. a) B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 2000, 122, 714-715;
6. b) B. M. Trost, J.-P. Surivet, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 15592-15602.
7. a) P. Cao, X. Zhang, Angew. Chem. 2000, 112, 4270-4272;
8. Angew. Chem. Int. Ed. 2000, 39, 4104-4106;
9. b) A. Lei, M. He, S. Wu, X. Zhang, Angew. Chem. 2002, 114, 3607-3610;
10. Angew. Chem. Int. Ed. 2002, 41, 3457-3460;
11. c) A. Lei, J. P. Waldkirch, M. He, X. Zhang, Angew. Chem. 2002, 114, 4708-4711;
12. Angew. Chem. Int. Ed. 2002, 41, 4526-4529;
13. d) A. Lei, M. He, X. Zhang, J. Am. Chem. Soc. 2002, 124, 8198-8199.
14. K. C. Nicolaou, D. L. F. Gray, T. Montagnon, S. T. Harrison, Angew. Chem. 2002, 114, 1038-1042;
15. Angew. Chem. Int. Ed. 2002, 41, 996-1000.
16. 6.
17. D. H. R. Barton, D. Crich, W. B. Motherwell, J. Chem. Soc. Chem. Commun. 1983, 939-941.
18. a) A. G. Myers, J. L. Gleason, T. Yoon, D. W. Kung, J. Am. Chem. Soc. 1997, 119, 656-673;
19. b) A. G. Myers, J. L. Gleason, T. Yoon, J. Am. Chem. Soc. 1995, 117, 8488-8489;
20. c) A. G. Myers, B. H. Yang, H. Chen, L. McKinstry, D. J. Kopecky, J. L. Gleason, J. Am. Chem. Soc. 1997, 119, 6496-6511.
21. For the one-step procedure to prepare the carboxylic acid 19, see: K. J. Shea, E. Wada, J. Am. Chem. Soc. 1982, 104, 5715-5719.
22. J. D. Olszewski, M. Marshalla, M. Sabat, R. J. Sundberg, J. Org. Chem. 1994, 59, 4285-4296.
23. t(major) = 24.55 min; a pseudoracemate of 23 was obtained through the same sequence of reactions using a 1:1 mixture of (R,R)- and (S,S)-pseudoephedrine in the acylation step.
24. For a review of the oxidation of phenolic compounds with hypervalent iodine reagents, see: a) R. M. Moriarty, O. Prakash, Org. React. 2001, 57, 327-415;
25. for more general reviews of the use of hypervalent iodine reagents in synthesis, see: b) T. Wirth, Angew. Chem. 2005, 117, 3722-3731;
26. Angew. Chem. Int. Ed. 2005, 44, 3656-3665;
27. c) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584;
28. d) R. M. Moriarty, O. Prakash, Org. React. 1999, 54, 273-418;
29. e) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178.
30. For selected examples of the use of carbon nucleophiles in the oxidative dearomatization of phenols, see: a) J. S. Swenton, A. Callinan, Y. Chen, J. J. Rohde, M. L. Kearns, G. W. Morrow, J. Org. Chem. 1996, 61, 1267-1274;
31. b) N. Lebrasseur, G.-J. Fan, M. Oxoby, M. A. Looney, S. Quideau, Tetrahedron 2005, 61, 1551-1562;
32. c) T. Honda, H. Shigehisa, Org. Lett. 2006, 8, 657-659;
33. d) H. Shigehisa, J. Takayama, T. Honda, Tetrahedron Lett. 2006, 47, 7301-7306.
34. Kita et al. have employed aminoquinones in similar reactions, however these processes may operate by oxidation of the amino group to provide an active electrophile, which reacts with a protected phenol nucleophile; see for example: a) Y. Kita, T. Yakura, H. Tohma, K. Kikuchi, Y. Tamura, Tetrahedron Lett. 1989, 30, 1119-1120;
35. b) Y. Kita, H. Tohma, M. Inagaki, K. Hatanaka, T. Yakura, J. Am. Chem. Soc. 1992, 114, 2175-2180;
36. c) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, T. Takada, J. Org. Chem. 1998, 63, 6625-6633.
37. a) S. Quideau, M. A. Looney, L. Pouységu, Org. Lett. 1999, 1, 1651-1654;
38. b) S. Quideau, L. Pouységu, M. Oxoby, M. A. Looney, Tetrahedron 2001, 57, 319-329.
39. [2] by using the method described for the preparation of 11 from 10.