Enantioselective total syntheses of trichodermamides A and B

Journal of the American Chemical Society

Volumn 130, Issue 51, 2008, Pages 17236-17237

  Wan, Xiaobo ^a   Joullié, Madeleine M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE TOTAL SYNTHESIS; EPOXIDE RING-OPENING REACTION; KEY REACTIONS; PEPTIDE COUPLING; QUINIC ACIDS; STEREOSELECTIVE CONSTRUCTION;

AMINES; NITROGEN COMPOUNDS;

SYNTHESIS (CHEMICAL);

HERBACEOUS AGENT; TRICHODERMAMIDE A; TRICHODERMAMIDE B; UNCLASSIFIED DRUG; DIPEPTIDE; EPOXIDE; OXAZINE DERIVATIVE; OXYGEN; PEPTIDE;

ARTICLE; CRYSTAL STRUCTURE; DEMETHYLATION; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; EPOXIDATION; OLEFINATION; CHEMICAL MODEL; CHEMISTRY; DRUG DESIGN; FUNGUS; HUMAN; IC 50; METABOLISM; METHODOLOGY; SYNTHESIS; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

CELL LINE, TUMOR; CHEMISTRY; CHEMISTRY, PHARMACEUTICAL; CRYSTALLOGRAPHY, X-RAY; DIPEPTIDES; DRUG DESIGN; EPOXY COMPOUNDS; FUNGI; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; OXAZINES; OXYGEN; PEPTIDES;

EID: 67849128248     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807011b     Document Type: Article

References (17)

1. Garo, E.; Starks, C. M.; Jensen, P. R.: Fenieal, W.; Lobkovsky, E.: Clardv, J. J Nat. Prod. 2003, 66, 423.
2. Seephonkai, P.; Kongsaeree, P.; Prabpai, S.; Isaka, M.; Thebtaranonth, Y. Org. Lett. 2006, 8, 3073.
3. Capon, R. J.; Ratnavake, R.; Stewart, M.; Lacey, E.; Tennant. S.; Gill. H. J. Qrg. Biomol. Chem. 2005, 3, 123.
4. Stipanovic, R. D.; Howell, C. R. J Antibiot. (Tokyo) 1982, 35, 1326.
5. Rether, J.; Serwe, A.; Anke, T.; Erkel, G. Biol. Chem. 2007, 388, 627.
6. Davis, R. A.; Longden, J.; Avery, V. M.; Healy, P. C. Bioorg. Med. Chem. Lett. 2008, 18. 2836.
7. Zakarian, A.; Lu, C.-D. J Am. Chem. Soc. 2006. 128, 5356.
8. Wan, X.; Doridot. G.; Joullie. M. M. Qrg. Lett. 2007, 9, 977.
9. Donald, J. R.; Edwards, M. G.; Tavlor, R. J. K. Tetrahedron Lett. 2007, 48, 5201.
10. Lu. C.-D.; Zakarian, A. Angew. Chem., Int. Ed. 2008. 47, 6829.
11. McKittriek, B. A.; Ganem, B. Tetrahedron Lett. 1985, 26, 4895.
12. Wipf, P.; Kim, Y.; Fritch, P. C. J.Org Chem. 1993, 58, 7195.
13. Yu, J. Q.; Corey, E. J. J. Am Chem. Soc. 2003, 125, 3232.
14. Catino, A. J.; Forslund. R. E.; Dovle, M. D. J Am Chem. Soc. 2004, 126, 13622.
15. Shing, T. K. M.; Yeung, Y. Y.; Su. P. L. Qrg. Lett. 2006, 8, 3149.
16. Salmond, W. G.; Barta. M. A.; Havens, J. L. J Org. Chem. 1978. 43. 2057.
17. Burlison, J. A.; Blagg, B. S. J.Org. Lett. 2006, 8, 4855.