Enantioselective total synthesis of the selective PI3 kinase inhibitor liphagal

Organic Letters

Volumn 12, Issue 20, 2010, Pages 4450-4453

  Alvarez Manzaneda, Enrique ^a   Chahboun, Rachid ^a   Alvarez, Esteban ^a   Cano, Ma José ^a   Haidour, Ali ^a   Alvarez Manzaneda, Ramón ^b  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF ALMERÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

LIPHAGAL; PHOSPHATIDYLINOSITOL 3 KINASE; TERPENE;

ARTICLE; CHEMICAL STRUCTURE; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

MOLECULAR STRUCTURE; PHOSPHATIDYLINOSITOL 3-KINASES; STEREOISOMERISM; TERPENES;

EID: 77957849105     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101173w     Document Type: Article

References (26)

1. For a recent review on marine natural products, see: Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2010, 27, 165
2. Marion, F.; Williams, D. E.; Patrick, B. O.; Hollander, I.; Mallon, R.; Kim, S. C.; Roll, D. M.; Feldberg, L.; Soest, R. W.; Andersen, R. J. Org. Lett. 2006, 8, 321
3. For recent reviews on the therapeutic potential of phosphoinositide-3- kinase inhibitors, see
4. Ward, S. G.; Sotsios, Y.; Dowden, J.; Bruce, I.; Finan, P. Chem. Biol. 2003, 10, 207
5. Ward, S. G.; Finan, P. Curr. Opin. Pharmacol. 2003, 3, 426
6. Grube, A.; Assmann, M.; Lichte, E.; Sasse, F.; Pawlik, J. R.; Köck, M. J. Nat. Prod. 2007, 70, 504
7. Mehta, G.; Likhite, N. S.; Kumar, C. S. A. Tetrahedron Lett. 2009, 50, 5260
8. Grube, A.; Assmann, M.; Lichte, E.; Sasse, F.; Pawlik, J. R.; Köck, M. J. Nat. Prod 2007, 70, 504
9. Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297
10. Okamura, W. H.; Peter, R.; Reischl, N. J. Am. Chem. Soc. 1985, 107, 1034
11. Schmidt, C.; Chisti, N. H.; Breining, T. Synthesis 1982, 391
12. Arima, Y.; Kinoshita, M.; Akita, H. Tetrahedro: Asymmetry 2007, 18, 1701
13. Akita, H.; Amano, H.; Kato, K.; Kinoshita, M. Tetrahedron: Asymmetry 2004, 15, 725
14. Tsangarakis, C.; Stratakis, M. Adv. Synth. Catal. 2005, 347, 1280
15. Polovinka, M. P.; Korchagina, D. V.; Gatilov, Y. V.; Bagrianskaya, I. Y.; Barkhash, V. A.; Perutskii, V. B.; Ungur, N. D.; Vlad, P. F.; Shcherbukhin, V. V.; Zefirov, N. S. J. Org. Chem. 1994, 59, 1509
16. Kuchkova, K. I.; Aryku, A. N.; Barba, A. N.; Vlad, P. F. Chem. Nat. Prod. 2007, 43, 412
17. Barrero, A. F.; Alvarez-Manzaneda, E.; Chahboun, R. Tetrahedron 1998, 54, 5635
18. Kulcitki, V.; Ungur, N.; Gavagnin, M.; Carbone, M.; Cimino, G. Eur. J. Org. Chem. 2005, 1816
19. Dominguez, G.; Hueso-Rodriguez, J. A.; de la Torre, M. C.; Rodriguez, B. Tetrahedron Lett. 1991, 32, 4765
20. Hagiwara, H.; Takeuchi, F.; Nozawa, M.; Hoshi, T.; Suzuki, T. Tetrahedron 2004, 60, 1983
21. Abad, A.; Agulló, C.; Castelblanque, L.; Cuñat, A. C.; Navarro, I.; Ramirez de Arellano, M. C. J. Org. Chem. 2000, 65, 4189
22. Tanimoto, H.; Oritani, T. Tetrahedron: Asymmetry 1996, 7, 1695
23. Alvarez-Manzaneda, E.; Chahboun, R.; Cabrera, E.; Alvarez, E.; Haidour, A.; Ramos, J. M.; Alvarez-Manzaneda, R.; Hmammouchi, M.; Es-Samti, H. Chem. Commun. 2009, 592
24. Hitotsuyanagi, Y.; Ichihara, Y.; Takeya, K.; Itokawa, H. Tetrahedron Lett. 1994, 35, 9401
25. Imakura, Y.; Konishi, T.; Uchida, K.; Sakurai, H.; Kobayashi, S.; Haruno, A.; Tajima, K.; Yamashita, S. Chem. Pharm. Bull. 1994, 42, 500
26. While this manuscript was in preparation, a similar approach to liphagal was published, see: George, J. H.; Baldwin, J. E.; Adlington, R. M. Org. Lett. 2010, 12, 2394