Synthesis and biological evaluation of (±)-dinemasone C and analogues

Journal of Organic Chemistry

Volumn 75, Issue 17, 2010, Pages 6057-6060

  Stewart, Amie M ^a   Meier, Kathrin ^b   Schulz, Barbara ^b   Steinert, Michael ^b   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTIONS; BIOLOGICAL EVALUATION; EPIMERIZATION; LEGIONELLA PNEUMOPHILA; RING FUSION;

CONDENSATION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

ANHYDRODINEMASONE BC; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; DINEMASONE B; DINEMASONE C; EPIDINEMASONE C; FUSIDILACTONE B; NOR DINEMASONE B; TAN 2483A; UNCLASSIFIED DRUG; WAOL A;

ALDOL REACTION; ALGA; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CYCLIZATION; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; EPOXIDATION; FUNGUS; LEGIONELLA PNEUMOPHILA; NONHUMAN;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACILLUS MEGATERIUM; BASIDIOMYCOTA; CHLORELLA; CYCLIZATION; ESCHERICHIA COLI; HETEROCYCLIC COMPOUNDS, 2-RING; LEGIONELLA PNEUMOPHILA; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 77956157838     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101408s     Document Type: Article

References (19)

1. Krohn, K.; Sohrab, Md. H.; van Ree, T.; Draeger, S.; Schulz, B.; Antus, S.; Kurtán, T. Eur. J. Org. Chem. 2008, 5638-5646
2. Krohn, K.; Biele, C.; Drogies, K.-H.; Steingröver, K.; Aust, H.-J.; Draeger, S.; Schulz, B. Eur. J. Org. Chem. 2002, 2331-2336
3. Qin, S.; Krohn, K.; Flörke, U.; Schulz, B.; Draeger, S.; Pescitelli, G.; Salvadori, P.; Antus, S.; Kurtán, T. Eur. J. Org. Chem. 2009, 3279-3284
4. Hayashi, K.; Takizawa, M.; Noguchi, K. Japanese Patent 10,287,679, 1998
5. Chem. Abstr. 1999, 130, 3122e.
6. Nozawa, O.; Okazaki, T.; Sakai, N.; Komurasaki, T.; Hanada, K.; Morimoto, S.; Chen, Z.-X.; He, B.-M.; Mizoue, K. J. Antibiot. 1995, 48, 113-118
7. Nazawa, O.; Okazaki, T.; Morimoto, S.; Chen, Z.-X.; He, B.-M.; Mizoue, K. J. Antibiot. 2000, 53, 1296-1300
8. Gao, X.; Snider, B. B. Org. Lett. 2003, 5, 451-454
9. Gao, X.; Snider, B. B. J. Org. Chem. 2004, 69, 5517-5527
10. The enolate formed from acetonide 12 cannot undergo elimination because the trans-fused acetonide locks the oxygen in a conformation that is orthogonal to the π electrons of the enolate. This constraint is absent with the alcohol groups of 11.
11. Prepared in a single step by hydrogenation of 4-hydroxy-6-methyl-2-pyrone over Raney nickel. Bacardit, R.; Moreno-Manas, M. Tetrahedron Lett. 1980, 21, 551-554
12. Fehr, M. J.; Consiglio, G.; Scalone, M.; Schmid, R. J. Org. Chem. 1999, 64, 5768-5776
13. Vogler, T.; Studer, A. Synthesis 2008, 1979-1993
14. Adam, W.; Michell, C. M.; Paredes, R.; Smerz, A. K.; Veloza, L. A. Liebigs Ann. Chem. 1997, 1365-1369
15. Adam, W.; Corma, A.; Reddy, T. I.; Renz, M. J. Org. Chem. 1997, 62, 3631-3637 See also: Mihelich, E. D. Tetrahedron Lett. 1979, 4729-4732
16. For the selective formation of an erythro epoxy alcohol from a 2,4-dienol, see: Conrow, R. E. Org. Lett. 2006, 8, 2441-2443
17. Sharpless, K. B.; Verhoeven, T. R. Aldrichim. Acta 1979, 12, 63-73
18. Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglas, G. G. A. J. Org. Chem. 1998, 63, 2342-2347
19. Schulz, B.; Sucker, J.; Aust, H.-J.; Krohn, K.; Ludewig, K.; Jones, P. G.; Döring, D. Mycol. Res. 1995, 99, 1007-1015