Stereoselective total synthesis of pachastrissamine (jaspine B)

Tetrahedron Letters

Volumn 49, Issue 6, 2008, Pages 980-983

  Passiniemi, Mikko ^a   Koskinen, Ari M P ^a  

^a AALTO UNIVERSITY   (Finland)

Author keywords

Cross metathesis; Cyclization; Enantioselective synthesis; Natural products; Pachastrissamine

Indexed keywords

ALDEHYDE; IODIDE; JASPINE A; PACHASTRISSAMINE; PALLADIUM; RUTHENIUM; SPHINGOSINE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; IODINATION; STEREOCHEMISTRY;

EID: 37849036459     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.014     Document Type: Article

References (52)

1. Newman D.J., and Cragg G.M. J. Nat. Prod. 70 (2007) 461-477
2. Chin Y.-W., Balunas M.J., Chai H.B., and Kinghorn A.D. AAPS J. 28 (2006) E239-E253
3. Lesney M.S. Today's Chemist at Work July (2004) 26-32
4. Feher M., and Schmidt J.M. J. Chem. Inf. Comput. Sci. 43 (2003) 218-227
5. Nicolaou K.C., and Yue E.W. Pure Appl. Chem. 69 (1997) 413-418
6. Nicolaou K.C. J. Org. Chem. 70 (2005) 7007-7027
7. Nicolaou K.C. J. Med. Chem. 48 (2005) 5613-5638
8. Nicolaou K.C., and Snyder S.A. Angew. Chem., Int. Ed. 44 (2005) 1012-1044
9. Breslow R. Chem. Soc. Rev. 1 (1972) 553-580
10. Faulkner D.J. Pure Appl. Chem. 48 (1976) 25-28
11. Johnson W.S. Bioorg. Chem. 5 (1976) 51-98
12. Van Tamelen E.E. Pure Appl. Chem. 53 (1981) 1259-1270
13. McDonald F.E., Towne T.B., and Schultz C.C. Pure Appl. Chem. 70 (1998) 355-358
14. Nicolaou K.C., Montagnon T., and Snyder S.A. Chem. Commun. (2003) 551-564
15. Valentine J.C., and McDonald F.E. Synlett (2006) 1816-1828
16. McDonald F.E., Tong R., Valentine J.C., and Bravo F. Pure Appl. Chem. 79 (2007) 281-291
17. Hoffmann R.W. Synthesis (2006) 3531-3541
18. Forke R., Krahl M.P., Krause T., Schlechtingen G., and Knölker H.-J. Synlett (2007) 268-272
19. Schmidt A.W., Olpp T., Schmid S., Goutal S., Jäger A., and Knölker H.-J. Synlett (2007) 1549-1552
20. Baran P.S., Maimone T.J., and Richter J.M. Nature 446 (2007) 404-408
21. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 40 (2001) 3726-3748
22. Schreiner P.R. Chem. Soc. Rev. 32 (2003) 289-296
23. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
24. de Figueiredo R.M., and Christmann M. Eur. J. Org. Chem. 16 (2007) 2575-2600
25. In: Kocovsky P., and Malkov A.V. (Eds). Organocatalysis in Organic Synthesis (2005), Elsevier B.V., Amsterdam, Netherlands 260
26. Kuroda I., Musman M., Ohtani I., Ichiba T., Tanaka J., Garcia Gravalos D., and Higa T. J. Nat. Prod. 65 (2002) 1505-1506
27. Ledroit V., Debitus C., Lavaud C., and Massiot G. Tetrahedron Lett. 44 (2003) 225-228
28. Sudhakar N., Ravi Kumar A., Prabhakar A., Jagadeesh B., and Venkateswara Rao B. Tetrahedron Lett. 46 (2005) 325-327
29. Bhaket P., Morris K., Stauffer C., and Datta A. Org. Lett. 7 (2005) 875-876
30. Du Y., Liu J., and Linhardt R. J. Org. Chem. 71 (2006) 1251-1253
31. van den Berg R., Boltje T., Verhagen C., Litjens R., Van der Marel G., and Overkleeft H. J. Org. Chem. 71 (2006) 836-839
32. Ribes C., Falomir E., Carda M., and Marco J. Tetrahedron 62 (2006) 5421-5425
33. Chandrasekhar S., Tiwari B., and Prakash S.J. ARKIVOC xi (2006) 155-161
34. Lee T., Lee S., Kwak Y.S., Kim D., and Kim S. Org. Lett. 9 (2007) 429-432
35. Reddy L.V.R., Reddy P.V., and Shaw A.K. Tetrahedron: Asymmetry 18 (2007) 542-546
36. Génisson Y., Lamandé L., Andrieu-Abadie N., Chantal A., and Baltas M. Tetrahedron: Asymmetry 18 (2007) 857-864
37. Prasad K.R., and Chandrakumar A. J. Org. Chem. 72 (2007) 6312-6315
38. Koskinen A.M.P., and Koskinen P.M. Tetrahedron Lett. 34 (1993) 6765-6768
39. Koskinen A.M.P., and Otsomaa L.A. Tetrahedron 53 (1997) 6473-6484
40. Koskinen A.M.P., and Kallatsa O. Tetrahedron 59 (2003) 6947-6954
41. Czernecki S., Georgoulis C., and Provelenghiou C. Tetrahedron Lett. (1976) 3535-3536
42. Kim K., Song Y., Lee B., and Hahn C. J. Org. Chem. 51 (1986) 404-407
43. 6Na) [M+Na] 402.1893, obsd: 402.1884.
44. Hara O., Fujii K., Hamada Y., and Sakagami Y. Heterocycles 54 (2001) 419-424
45. Burke S., and Jiang L. Org. Lett. 3 (2001) 1953-1955
46. Jiang L., and Burke S. Org. Lett. 4 (2002) 3411-3414
47. 4Na) [M+Na] 342.1681, obsd: 342.1689.
48. Blackwell H., O'Leary D., Chatterjee A., Washenfelder R., Bussman D.A., and Grubbs R. J. Am. Chem. Soc. 122 (2000) 58-71
49. Rai A., and Basu A. Org. Lett. 6 (2004) 2861-2863
50. Rai A., and Basu A. J. Org. Chem. 70 (2005) 8228-8230
51. Lera M., and Hayes C. Org. Lett. 3 (2001) 2765-2768
52. 4Na) [M+Na] 510.3559, obsd: 510.3580.