Total synthesis of asperlicin D

Tetrahedron Letters

Volumn 47, Issue 5, 2006, Pages 693-694

  Al Said, Naim H ^a   Al Qaisi, Lina S ^a  

^a JORDAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Jordan)

Author keywords

Cyclodehydration; Intramolecular aza Wittig; Linear tripeptide; Synthesis of asperlicin D

Indexed keywords

ASPERLICIN D; CHOLECYSTOKININ RECEPTOR BLOCKING AGENT; TRIPEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEHYDRATION; DRUG STRUCTURE; DRUG SYNTHESIS; QUANTUM YIELD; SUBSTITUTION REACTION; WITTIG REACTION;

EID: 29544436388     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.123     Document Type: Article

References (21)

1. H.H. Sum, C.J. Barrow, D.M. Sedlock, A.M. Gillum, and R. Cooper J. Antibiot. 47 1994 515 522
2. L. Rahbek, J. Breinholt, J.C. Frisvad, and C. Christophersen J. Org. Chem. 74 1994 1789 1792
3. L. Rahbek, and J. Breinholt J. Nat. Prod. 72 1999 904 905
4. J.R. Dia, B.K. Carte, P.J. Sidebottom, A.L.S. Yew, Y. Huang, and M.S. Butler J. Nat. Prod. 74 2001 125 126
5. R.S.L. Chang, V.J. Lotti, R.L. Monaghan, J. Birnbaum, E.O. Stapley, M.A. Goetz, and J.P. Albers-Schorberg Science 230 1985 177 179
6. J.M. Liesch, O.D. Hensen, and M.A. Goetz J. Antibiot. 41 1988 878 881
7. B.K. Joshi, J.B. Gloer, and D.T. Wicjlow J. Nat. Prod. 72 1999 650 652
8. F. He, B.M. Foxman, and B.B. Snider J. Am. Chem. Soc. 120 1998 6417 6418
9. T. Sugimori, T. Okawa, S. Eguchi, A. Kakehi, E. Yashima, and Y. Okamoto Tetrahedron 54 1998 7997 8008
10. N.H. Al-Said, and Z.N. Ishtaiwi Acta. Chim. Slov. 52 2005 328 331
11. P. Wipf, and C.P. Miller J. Org. Chem. 58 1993 3604 3606
12. 2 406).
13. (cat) for 3 h. The reaction mixture was concentrated and purified as in part a to afford 1 (0.251 g, 62%).
14. For reviews on aza-Wittig reactions see: S. Eguchi ARKIVOC 2005 98 119
15. Y.G. Gololobov Tetrahedron 48 1992 1353 1407 and references cited therein
16. See for example: B.B. Snider, and M.V. Busuyek Tetrahedron 5 2001 3301 3307
17. P. Molina, P.M. Fresneda, and S. Delgado Synthesis 1999 327 329
18. P. Molina, M. Aljarin, and A. Vidal Tetrahedron 45 1989 4273 4287
19. T. Sugimori, T. Okawa, S. Eguchi, A. Kakehi, E. Yashima, and Y. Okamoto Tetrahedron 54 1998 7997 8008
20. S. Eguchi, K. Ymashita, Y. Matsushita, and A. Kakehi J. Org. Chem. 70 1995 4007 4012
21. P. Molina, I. Diaz, and A. Tarraga Tetrahedron 51 1995 5717 5730