Absolute stereochemistry of the diepoxins

Tetrahedron

Volumn 52, Issue 2, 1996, Pages 435-446

  Schlingmann, Gerhard ^a,b   Matile, Stefan ^a   Berova, Nina ^a   Nakanishi, Koji ^a   Carter, Guy T ^a,b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b WYETH RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DECALIN DERIVATIVE; DIEPOXIN; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; DRUG ISOLATION; DRUG STRUCTURE; FUNGUS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY DIFFRACTION;

FUNGI;

EID: 0030063595     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00923-X     Document Type: Article

References (23)

1. Schlingmann, G., Milne, L.; Pearce, C.P.; Borders, D.B.; Greenstein, M.; Maiese, W.M.; Carter, G.T.; J. Antibiot., 1995, 48(5), 375-9
2. a) Schlingmann, G., West, R.R.; Milne, L.; Pearce, C.P.; Carter, G.T.; Tetrahedron Lett. 1993, 34(45), 7225-8.
3. rd Interscience Conference on Antimicrob. Agents and Chemotherapy (ICAAC), Abstr. 578
4. a) Weber, H.A.; Baenziger, N.C.; Gloer, J. B.; J. Am. Chem. Soc. 1990, 112, 6718-9.
5. b) Weber, H.A.; Gloer, J. B.; J. Org. Chem. 1991, (56) 4355-60
6. Singh, S.B.; Zink, D.L.; Liesch, J.M.; Ball, R.G.; Goetz, M.A.; Bolessa, E.A.; Giacobbe, R.A.; Silverman, K.C.; Bills, G.F.; Pelaez, F.; Cascales, C.; Gibbs, J.B.; Lingham, R.B.; J. Org.Chem. 1994, (59) 6296-302
7. a) Krohn, K.; Michel, A.; Flörke, U.; Aust H.-J.; Draeger, S.; Schulz, B.; Liebigs Ann. Chem. 1994, (11) 1093-7.
8. b) Krohn, K.; Michel, A.; Flörke, U.; Aust H.-J.; Draeger, S.; Schulz, B.; Liebigs Ann. Chem. 1994, (11) 1099-108.
9. a) Chu, M.; Truumees, I.; Patel, M.G.; Gullo V.P.; Blood, C.; King, I.; Pai, J.-K.; Puar, M.S.; Tetrahedron Lett. 1994, 35, 1343-6.
10. b) Chu, M.; Truumees, I.; Patel, M.G.; Gullo, V.P.; Puar, M.S.; McPhail, A. T. J. Org. Chem. 1994, 59, 1222-3.
11. c) Chu, M.; Gullo V.P.; Horan, A.C.; Patel, M.G.; Patent WO 93-US2737 930401. US 92-864291 920406.
12. a) Thiergardt, R.; Hug, P.; Rihs, G.; Peter, H.H.; Tetrahedron Lett. 1994, 35(7), 1043-6.
13. b) Petersen, F.; Moerker, T.; Vanzanella, F.; Peter, H.H.; J. Antibiot. 1994, 47(10), 1098-103.
14. Thiergardt, R; Rihs, G.; Hug, P.; Peter, H.H.; Tetrahedron 1995, 51(3), 733-42.
15. a) Yamashita, K.; Takaiwa, A.; Nakada, H.; Agric. Biol. Chem. 1980, 44(12), 2931-5.
16. b) Anke, H.; Schwab, H.; Achenbach, H.; J. Antibiot. 1980, 33(9), 931-39.
17. c) Clemo, N.; Pattenden, G.; Tetrahedron Lett. 1982, 23(5),589-92.
18. Tsuzuki, K.; Iwai, Y.; Omura, S., Shimizu, H.; Kitajima, N.; J. Antibiot. 1986, 39(9), 1343-5.
19. a) Harada, N.; Nakanishi, K.; Circular Dichroic Spectroscopy-Excition Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA 1983.
20. b) Nakanishi, K.; Berova N.; Woody, R.W.; Circular Dichroism-Principles and Applications; VCH Publishers Inc., New York, NY, 1994.
21. Cai, G.; Bozhkova, N.; Odingo, J.; Berova, N.; K. Nakanishi; J. Am. Chem. Soc. 1993, 115, 7192-8.
22. Harada N.; Uda, H.; J. Chem. Soc. Chem. Commun. 1982, 230.
23. The triazole was prepared following the protocol of Cai, et al in Ref. 12.