A concise synthesis of bengamide E and analogues via E-selective cross-metathesis olefination

Synlett

Volumn , Issue 19, 2010, Pages 2923-2927

  Alam, Safiul ^a   Dhimane, Hamid ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

analogues; bengamide; cross metathesis; isomerization; stereoselective olefination

Indexed keywords

1,4 BENZOQUINONE; ALKENE; ANTINEOPLASTIC AGENT; BENGAMIDE DERIVATIVE; BENGAMIDE E; GLUCURONOLACTONE; LAF 389; METHIONYL AMINOPEPTIDASE; POLYKETIDE; PROTEIN TYROSINE KINASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; ISOMERIZATION; OLEFINATION; PROTON NUCLEAR MAGNETIC RESONANCE; PYROLYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TUMOR GROWTH;

EID: 78650179460     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259015     Document Type: Article

References (36)

1. Quiñoà E, Adamczeski M, Crews P, Bakus G, J. Org. Chem. 1986 51 4494
2. Adamczeski M, Quiñoà E, Crews P, J. Am. Chem. Soc. 1989 111 647
3. Adamczeski M, Quiñoà E, Crews P, J. Org. Chem. 1990 55 240
4. DAuria M V., Giannini C, Minale L, Zampella A, Debitus C, Frostin M, J. Nat. Prod. 1997 60 814
5. Thale Z, Kinder F R., Bair K W., Bontempo J, Czuchta A M., Versace R W., Phillips P E., Sanders M L., Wattanasin S, Crews P, J. Org. Chem. 2001 66 1733
6. For recent review (up to early 2001), see:, Kinder F R., Org. Prep. Proced. Int. 2002 34 559
7. Banwell M G., McRae K J., J. Org. Chem. 2001 66 6768
8. Liu W, Szewczyk J M., Waykole L, Repic O, Blacklock T J., Tetrahedron Lett. 2002 43 1373
9. Boeckman R K. Jr., Clark T J., Shook B C., Org. Lett. 2002 4 2109
10. Sarabia F, Sánchez-Ruiz A, J. Org. Chem. 2005 70 9514; and references cited therein
11. Liu G, Ma Y.-M, Tai W.-Y, Xie C.-M, Li Y.-L, li J, Nan F.-J, ChemMedChem 2008 3 74
12. Kinder F R., Versace R W., Bair K W., Bontempo J M., Cesarz D, Chen S, Crews P, Czuchta A M., Jagoe C T., Mou Y, Nemzek R, Phillips P E., Tran L D., Wang R, Weltchek S, Zabludoff S, J. Med. Chem. 2001 44 3692
13. Towbin H, Bair K W., DeCaprio J A., Eck M J., Kim S, Kinder F K., Morollo A, Mueller D R., Schindler P, Song H K., vanOostrum J, Versace R W., Voshol H, Wood J, Zabludoff S, Phillips P E., J. Biol. Chem. 2003 278 52964
14. For recent reviews, see:, Bernier S G., Taghizadeh N, Thompson C D., Westlin W F., Hannig G, J. Cell. Biochem. 2005 95 1191
15. Selvakumar P, Lakshmikuttyamma A, Dimmock J, Sharma R K., Biochim. Biophys. 2006 1765 148
16. Frottin F, Martinez A, Peynot P, Mitra S, Holz R C., Giglione C, Meinel T, Mol. Cell. Proteomics 2006 5 2336
17. Wiltschi B, Merkel L, Budisa N, ChemBioChem 2009 10 217
18. Hu X, Dang Y, Tenney K, Crews P, Tsai C W., Sixt K M., Cole P A., Liu J O., Chem. Biol. 2007 14 764
19. Levraud C, Calvet-Vitale S, Bertho G, Dhimane H, Eur. J. Org. Chem. 2008 1901
20. David M, Dhimane H, Synlett 2004 1029
21. Xu D D., Waykole L, Calienni J V., Ciszewski L, Lee G T., Liu W, Szewczyk J, Vargas K, Prasad K, Repic O, Blacklock T J., Org. Process Res. Dev. 2003 7 856
22. Grank G, Eastwood F W., Aust. J. Chem. 1964 17 1392
23. Ando M, Ohhara H, Takase K, Chem. Lett. 1986 879
24. Chatterjee A K., Choi R.-L, Sanders D P., Grubbs R H., J. Am. Chem. Soc. 2003 125 11360
25. Maynard H D., Grubbs R H., Tetrahedron Lett. 1999 40 4137
26. Edwards S D., Lewis T, Raylor R J. K., Tetrahedron Lett. 1999 40 4267
27. Bourgeois D, Pancrazi A, Ricard L, Prunet J, Angew. Chem. Int. Ed. 2000 39 725
28. Fürstner A, Thiel O R., Ackermann L, Schanz H.-J, Nolan S P., J. Org. Chem. 2000 65 2204
29. For review, see:, Schmidt B, Eur. J. Org. Chem. 2004 1865
30. Alcaide B, Almendros P, Chem. Eur. J. 2003 9 1259
31. Cadot C, Dalko P I., Cossy J, Tetrahedron Lett. 2002 43 1839
32. Maishal T K., Sinha-Mahapatra D K., Paranjape K, Sarkar A, Tetrahedron Lett. 2002 43 2263
33. Courchay F C., Sworen J C., Ghiviriga I, Aboud K A., Wagener K B., Organometallics 2006 25 6074; and references cited therein
34. Hong S H., Sanders D P., Lee C W., Grubbs R H., J. Am. Chem. Soc. 2005 127 17160
35. Boyle W J. Jr., Sifniades S, vanPeppen J F., J. Org. Chem. 1979 44 4841
36. Liu W, Xu D D., Repic O, Blacklock T J., Tetrahedron Lett. 2001 42 2439