A concise total synthesis of salinosporamide A

Organic and Biomolecular Chemistry

Volumn 4, Issue 15, 2006, Pages 2845-2846

  Mulholland, Nicholas P ^a   Pattenden, Gerald ^a   Walters, Iain A S ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; ALDEHYDES; CATALYSIS; DERIVATIVES; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

INTRAMOLECULAR CYCLISATION; REGIOSELECTIVE REDUCTION; SALINOSPORAMIDE A;

NITROGEN COMPOUNDS;

LACTONE; PROTEASOME; PROTEINASE INHIBITOR; PYRROLE DERIVATIVE; SALINOSPORAMIDE A;

ARTICLE; CYCLIZATION; DRUG ANTAGONISM; SYNTHESIS;

CYCLIZATION; LACTONES; PROTEASE INHIBITORS; PROTEASOME ENDOPEPTIDASE COMPLEX; PYRROLES;

EID: 33746215875     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b607109k     Document Type: Article

References (29)

1. R. H. Feling G. O. Buchanan T. J. Mincer C. A. Kauffman P. R. Jensen W. Fenical Angew. Chem., Int. Ed. 2003 42 355 357
2. E. J. Corey W.-D. Z. Li Chem. Pharm. Bull. 1999 47 1 10
3. E. J. Corey G. A. Reichard R. Kania Tetrahedron Lett. 1993 34 6977 6980
4. E. J. Corey G. A. Reichard J. Am. Chem. Soc. 1992 114 10677 10678
5. G. Fenteany R. F. Standaert G. A. Reichard E. J. Corey S. L. Schreiber Proc. Natl. Acad. Sci. U. S. A. 1994 91 3358 3362
6. S. Omura T. Fujimoto K. Otoguro K. Matsuzaki R. Moriguchi H. Tanaka Y. Sasaki J. Antibiot. 1991 44 113 116
7. S. Omura K. Matsuzaki T. Fujimoto K. Kosuge T. Furuya S. Fujita A. Nakagawa J. Antibiot. 1991 44 117 118
8. J. S. Panek C. E. Masse A. J. Morgan J. Adams Eur. J. Org. Chem. 2000 2513 2528
9. T. J. Donohoe H. O. Sintim L. Sisangia K. W. Ace P. M. Guyo A. Cowley J. D. Harling Chem.-Eur. J. 2005 11 4227 4238
10. T. J. Donohoe H. O. Sintim L. Sisangia J. D. Harling Angew. Chem., Int. Ed. 2004 43 2293 2269
11. H. Ooi N. Ishibashi Y. Iwabuchi J. Ishihara S. Hatekeyama J. Org. Chem. 2004 69 7765 7768
12. J. J. Wardrop E. G. Bowen Chem. Commun. 2005 5106 5108
13. C. J. Hayes A. E. Sherlock M. D. Selby Org. Biomol. Chem. 2006 4 193 195
14. N. Fukuda K. Sasaki T. V. R. S. Sastry M. Kanai M. Shibasaki J. Org. Chem. 2006 71 1220 1225
15. L. R. Reddy P. Saravanan E. J. Corey J. Am. Chem. Soc. 2004 126 6230 6231
16. L. R. Reddy J.-F. Fournier B. V. S. Reddy E. J. Corey Org. Lett. 2005 7 2699 2701
17. L. R. Reddy J.-F. Fournier B. V. S. Reddy E. J. Corey J. Am. Chem. Soc. 2005 127 8974 8976
18. A. Endo S. J. Danishefsky J. Am. Chem. Soc. 2005 127 8298 8299
19. J. K. Thottathil J. L. Moniot R. H. Mueller M. K. T. Wong T. P. Kissick J. Org. Chem. 1986 51 3140 3143
20. Y. Hamada A. Kawai Y. Kohno O. Hara T. Shioiri J. Am. Chem. Soc. 1989 111 1524 1525
21. Y. Hamada O. Hara A. Kawai Y. Kohno T. Shioiri Tetrahedron 1991 47 8635 8652
22. C. J. Brennan G. Pattenden G. Rescourio Tetrahedron Lett. 2003 44 8757 8760
23. A. Nakagawa S. Takahashi K. Uchida K. Matsuzaki S. mura A. Nakamura N. Kurihara T. Nakamatsu Y. Miyake K. Take M. Kainosho Tetrahedron Lett. 1994 35 5009 5012
24. M. Lee D. H. Kim Bioorg. Med. Chem. 2002 10 913 922
25. G. Simig G. Doleschall G. Hornyák J. Fetter K. Lempert J. Nyitrai P. Huszthy T. Gizur M. Kajtár-Peredy Tetrahedron 1985 41 479 484
26. 2 (all data) = 0.123. CCDC reference number 608046. For crystallographic data in CIF or other electronic format see DOI: 10.1039/b607109k
27. A small amount (<10%) of the corresponding O-TMS epimer was produced concurrently, resulting from a retro-aldolisation process. The epimer was cleanly removed by chromatography
28. 2Me in 8b to reduction, as a consequence of their antiplanar relationship
29. 7SiNa requires 632.3014)