Enantioselective synthesis of the tetracyclic core of platensimycin

Synthesis

Volumn , Issue 10, 2011, Pages 1532-1536

  Ueda, Yohei ^a   Iwahashi, Kayoko ^a   Iguchi, Kazuo ^a   Ito, Hisanaka ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

antibiotics; enantioselective hydrogenation; formal synthesis; iodoetherification

Indexed keywords

ENANTIOSELECTIVE HYDROGENATION; ENANTIOSELECTIVE SYNTHESIS; FORMAL SYNTHESIS; IODOETHERIFICATION; OPTICALLY ACTIVE FORM; P-ANISALDEHYDE; PROTECTING GROUP;

1,7 DIHYDROXY 3 (1 METHYLETHENYL) 1,2,3,4 TETRAHYDRONAPHTHALENE; 10 METHYL 11 OXA 4 OXO TETRACYCLO[7.2.1.1.0]TRIDECA 2(3),5 DIENE; 3 (DIMETHYLHYDROXYMETHYL) 7 HYDROXY 1 TETRALONE; 3 (METHOXYCARBONYL) 4 (4 METHOXYPHENYL)BUT 3 ENOIC ACID; 3 (METHOXYCARBONYL) 4 (4 METHOXYPHENYL)BUTANOIC ACID; 4 HYDROXY 10 IODOMETHYL 10 METHYL 11 OXATRICYCLO[7.2.0]DODECA 2,4,6 TRIENE; 7 HYDROXY 3 (1 METHYLETHENYL) 1 TETRALONE; METHYL (6 HYDROXY 4 OXO 1,2,3,4 TETRAHYDRONAPHTHALEN 2 YL)CARBOXYLIC ACID; METHYL (6 METHOXY 4 OXO 1,2,3,4 TETRAHYDRONAPHTHALEN 2 YL)CARBOXYLIC ACID; PLATENSIMYCIN; UNCLASSIFIED DRUG;

ARTICLE; BROMOETHERIFICATION; CHEMICAL BOND; CYCLIZATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ETHERIFICATION; FRIEDEL CRAFTS REACTION; IODOETHERIFICATION; STEREOCHEMISTRY;

EID: 79955844784     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260002     Document Type: Article

References (34)

1. Wang J, Soisson S M., Young K, Shoop W, Kodali S, Galgoci A, Painter R, Parthasarathy G, Tang Y S., Cummings R, Ha S, Dorso K, Motyl M, Jayasuriya H, Ondeyka J, Herath K, Zhang C, Hernandez L, Allocco J, Basilio A, Tormo J R., Genilloud O, Vicente F, Pelaez F, Colwell L, Lee S H., Michael B, Felcetto T, Gill C, Silver L L., Hermes J D., Bartizal K, Barrett J, Schmatz D, Becker J W., Cully D, Singh S B., Nature 2006 441 358
2. Singh S B., Jayasuriya H, Ondeyka J G., Herath K B., Zhang C, Zink D L., Tsou N N., Ball R G., Basilio A, Genilloud O, Diez M T., Vicente F, Pelaez F, Young K, Wang J, J. Am. Chem. Soc. 2006 128 11916
3. Nicolaou K C., Li A, Edmonds D J., Angew. Chem. Int. Ed. 2006 45 7086
4. Nicolaou K C., Edmonds D J., Li A, Tria G S., Angew. Chem. Int. Ed. 2007 46 3942
5. Zou Y, Chen C.-H, Taylor C D., Foxman B M., Snider B B., Org. Lett. 2007 9 1825
6. Kaliappan K P., Ravikumar V, Org. Lett. 2007 9 2417
7. Nicolaou K C., Tang Y, Wang J, Chem. Commun. 2007 1922
8. Li P, Payette J N., Yamamoto H, J. Am. Chem. Soc. 2007 129 9534
9. Ghosh A K., Xi K, Org. Lett. 2007 9 4013
10. Tiefenbacher K, Mulzer J, Angew. Chem. Int. Ed. 2007 46 8074
11. Lalic G, Corey E J., Org. Lett. 2007 9 4921
12. Heretsch P, Giannis A, Synthesis 2007 2614
13. Nicolaou K C., Pappo D, Tsang K Y., Gibe R, Chen D Y.-K, Angew. Chem. Int. Ed. 2008 47 944
14. Kim C H., Jang K P., Choi S Y., Chung Y K., Lee E, Angew. Chem. Int. Ed. 2008 47 4009
15. Matsuo J, Takeuchi K, Ishibashi H, Org. Lett. 2008 10 4049
16. Ghosh A K., Xi K, J. Org. Chem. 2009 74 1163
17. Nicolaou K C., Li A, Ellery S P., Edmonds D J., Angew. Chem. Int. Ed. 2009 48 6293
18. Yun S Y., Zheng J.-C, Lee D, J. Am. Chem. Soc. 2009 131 8413
19. McGrath N A., Bartlett E S., Sittihan S, Njardarson J T., Angew. Chem. Int. Ed. 2009 48 8543
20. Nicolaou K C., Li A, Edmonds D J., Tria G S., Ellery S P., J. Am. Chem. Soc. 2009 131 16905
21. Tiefenbacher K, Tröndlin L, Mulzer J, Pfaltz A, Tetrahedron 2010 66 6508
22. Xing S, Pan W, Liu C, Ren J, Wang Z, Angew. Chem. Int. Ed. 2010 49 3215
23. Eey S T.-C, Lear M J., Org. Lett. 2010 12 5510
24. Magnus P, Rivera H, Lynch V, Org. Lett. 2010 12 5677
25. Beaulieu M.-A, Sabot C, Achache N, Guérard K C., Canesi S, Chem. Eur. J. 2010 16 11224
26. Hirai S, Nakada M, Tetrahedron 2011 67 518
27. For reviews on the synthetic approaches to platensimycin, see:, Tiefenbacher K, Mulzer J, Angew. Chem. Int. Ed. 2008 47 2548
28. Harsh P, ODoherty G A., Chemtracts 2009 22 31
29. Palanichamy K, Kaliappan K P., Chem. Asian J. 2010 5 668
30. Lu X, You Q, Curr. Med. Chem. 2010 17 1139
31. Caro Y, Torrado M, Masaguer C F., Raviéa E, Tetrahedron: Asymmetry 2003 14 3689
32. Kometani T, Shiotani S, J. Med. Chem. 1978 21 1105
33. Tang W, Liu D, Zhang X, Org. Lett. 2003 5 205
34. Burgess E M., J. Org. Chem. 1973 38 26