Total synthesis of (±)-batzelladine K: A biomimetic approach

Synthesis

Volumn , Issue 15, 2010, Pages 2567-2570

  Ahmed, Nafees ^a   Brahmbhatt, Keyur G ^a   Singh, Inder Pal ^a   Bhutani, Kamlesh K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

batzelladines; biomimetic synthesis; marine natural products; phosphorane; tricyclic guanidine

Indexed keywords

BIOMIMETIC SYNTHESIS; KEY REACTIONS; MARINE NATURAL PRODUCTS; PHOSPHORANES; TOTAL SYNTHESIS; UNSATURATED KETONES; WITTIG REACTION;

ALDEHYDES; KETONES; STEREOCHEMISTRY;

BIOMIMETICS;

ALDEHYDE; ALKALOID; BATZELLADINE K; GUANIDINE; KETONE; PHOSPHORANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; POLYMERIZATION; STEREOCHEMISTRY; WITTIG REACTION;

EID: 77954916628     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218822     Document Type: Article

References (38)

1. (a)Berlinck R G. S., Nat. Prod. Rep. 1996 13 377
2. (b)Berlinck R G. S., Nat. Prod. Rep. 1999 16 339
3. (c)Berlinck R G. S., Nat. Prod. Rep. 2002 19 617
4. (d)Berlinck R G. S., Kossuga M H., Nat. Prod. Rep. 2005 22 516
5. (e)Berlinck R G. S., Burtoloso A C. B., Kossuga M H., Nat. Prod. Rep. 2008 25 919
6. (f)Heys L, Moore C G., Murphy P J., Chem. Soc. Rev. 2000 29 57
7. Patil A D., Kumar N V., Kokke W C., Bean M F., Freyer A J., Brosse C D., Mai S, Truneh A, Faulkner D J., Cart B, Breen A L., Hertzberg R P., Johnson R K., Westley J W., Potts B C. M., J. Org. Chem. 1995 60 1182
8. Patil A D., Freyer A J., Taylor P B., Carte B, Zuber G, Johnson R K., Faulkner D J., J. Org. Chem. 1997 62 1814
9. Gallimore W A., Kelly M, Scheuer P J., J. Nat. Prod. 2005 68 1420
10. Hua H M., Peng J, Dunbar D C., Schinazi R F., Andrews A G. D. C., Cuevas C, Garcia-Fernandez L F., Kelly M, Hamann M T., Tetrahedron 2007 63 11179
11. (a)Snider B B., Chen J, Patil A D., Freyer A J., Tetrahedron Lett. 1996 37 6977
12. (b)RamaRao A V., Gurjar M K., Vasudevan J, J. Chem. Soc., Chem. Commun. 1995 1369
13. (c)Black G P., Murphy P J., Walshe N D. A., Hibbs D E., Hursthouse M B., AbdulMalik K M., Tetrahedron Lett. 1996 37 6943
14. (d)Elliott M C., Long M S., Tetrahedron Lett. 2002 43 9191
15. (e)Elliott M C., Long M S., Org. Biomol. Chem. 2004 2 2003
16. (f)Black G P., Murphy P J., Thornhill A J., Walshe N D. A., Zanetti C, Tetrahedron 1999 55 6547
17. (g)Davies C D., Elliott M C., Hill-Cousins J, Khan M A., Maqbool T, Wood J L., Synlett 2008 2028
18. Black G P., Murphy P J., Walshe N D. A., Tetrahedron 1998 54 9481
19. (a)Arnold M A., Day K A., Duron S G., Gin D Y.,J. Am. Chem. Soc. 2006 128 13255
20. (b)Shimokawa J, Shirai K, Tanatani A, Hashimoto Y, Nagasawa K, Angew. Chem. Int. Ed. 2004 43 1559
21. Shimokawa J, Ishiwata T, Shirai K, Koshino H, Tanatani A, Nakata T, Hashimoto Y, Nagasawa K, Chem. Eur. J. 2005 11 6878
22. Collins S K., McDonald A I., Overman L E., Rhee Y H., Org. Lett. 2004 6 1253
23. (a)Cohen F, Overman L E., Sakata S K., Org. Lett. 1999 1 2169
24. (b)Evans P A., Qin J, Robinson J E., Bazin B, Angew. Chem. Int. Ed. 2007 46 7417
25. (c)Ishiwata T, Hino T, Koshino H, Hashimoto Y, Nakata T, Nagasawa K, Org. Lett. 2002 4 2921
26. Snider B B., Chen J, Tetrahedron Lett. 1998 39 5697
27. (a)Cohen F, Overman L E., J. Am. Chem. Soc. 2001 123 10782
28. (b)Cohen F, Overman L E., J. Am. Chem. Soc. 2006 128 2604
29. Bewley C A., Ray S, Cohen F, Collins S K., Overman L E., J. Nat. Prod. 2004 67 1319
30. (a)Brahmbhatt K G., Ahmed N, Singh I P., Bhutani K K., Tetrahedron Lett. 2009 50 5501
31. (b)Ahmed N, Brahmbhatt K G., Singh I P., Bhutani K K., J. Heterocycl. Chem. 2010 DOI: 10.1002/jhet.364
32. (c)Chauthe S K., Bharate S B., Sabde S, Mitra D, Bhutani K K., Singh I P., Bioorg. Med. Chem. 2010 18 2029
33. (d)Singh I P., Bharate S B., Bhutani K K., Curr. Sci. 2005 89 269
34. (e)Ahmed N, Brahmbhatt K G., Sabde S, Mitra D, Singh I P., Bhutani K K., Bioorg. Med. Chem. 2010 18 2872
35. Yu M, Pochapsky S S., Snider B B., J. Org. Chem. 2008 73 9065
36. Sekine M, Iijima Y, Iwamoto O, Nagasawa K, Heterocycles 2010 80 395
37. House H O., Cronin T H., J. Org. Chem. 1965 30 1061
38. Murphy P J., Williams H L., Hibbs D E., Hursthouse M B., AbdulMalik K M., Tetrahedron 1996 52 8315