cis-decalins from quinic acid: Toward a synthesis of branimycin

Organic Letters

Volumn 9, Issue 5, 2007, Pages 813-816

  Marchart, Stefan ^a   Mulzer, Johann ^a   Enev, Valentin S ^a  

^a Institut fur Organische Chemie   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

BRANIMYCIN; DECALIN; EPOXIDE; KETONE; MACROLIDE; NAPHTHALENE DERIVATIVE; QUINIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

EPOXY COMPOUNDS; KETONES; MACROLIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHALENES; QUINIC ACID;

EID: 33947162951     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0630189     Document Type: Article

References (34)

1. Enev, V. S.; Drescher, M.; Kaehlig, H.; Mulzer, J. Synlett 2005, 14, 2227-2229.
2. Felzmann, W.; Arion, V. B.; Mieusset, J. L.; Mulzer, J. Org. Lett. 2006, 8, 3849-3851.
3. (a) Review: Kallmerten, J. Studies in Natural Procducts Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 1995; Vol. 17, pp 283-310 and references cited therein,
4. (b) Celmer, W. D.; Chmurny, C. N.; Moppett, C. E.; Ware, R. S.; Watts, P. C.; Whipple, E. B. J. Am. Chem. Soc. 1980, 102, 4203-4209.
5. (c) Tone, J.; Shibakawa, R.; Maeda, H.; Yamauchi, Y.; Niki, K.; Saito, M.; Tsukuda, K.; Whipple, E. B.; Watts, P. C.; Moppett, C. E.; Jefferson, M. T.; Huang, L. H.; Cullen, W. P.; Celmer, W. D. 20th Interscience Conference on Antimicrobial Agents and Chemotherapy, New Orleans, LA, Abstract 62, Sep 22-24, 1980.
6. Speitling, M.; Grün-Wollny, I.; Hannske, F. G.; Laatsch, H. 12 and 13 IRSEER Naturstofftage der DECHEMA e. V. Irsee, 2000 and 2001.
7. (a) Barco, A.; Benetti, S.; De Risi, C.; Marchetti, P.; Pollini, G. P.; Zanirato, V. Tetrahedron: Asymmetry 1997, 8, 3515-3545.
8. (b) Usami, Y.; Ueda, Y. Chem. Lett. 2005, 34, 1062-1063.
9. Fürstner A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
10. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
11. Trinka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
12. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
13. Lee, C. W.; Grubbs, R. H. Org. Lett. 2000, 2, 2145-2147.
14. Gaich, T.; Mulzer, J. Curr. Top. Med. Chem. 2005, 5, 1473-1494.
15. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527.
16. Paquette, L. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 5, pp 785-898.
17. Murray, L. M.; O'Brien, P.; Taylor, R. J. K. Org. Lett. 2003, 5, 1943-1946.
18. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 13, 4259-4275.
19. (a) Murray, L. M.; O'Brien, P.; Taylor, R. J. K. Org. Lett. 2003, 5, 1943-1946.
20. (b) Mathews, R. S.; Girgenti, S. J.; Folkers, E. A. J. Chem. Soc., Chem. Commun. 1970, 708-709.
21. (c) House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 1000-1003.
22. (d) Skaddan, M. B.; Wüst, F. R.; Katzenellenbogen, J. A. J. Org. Chem. 1999, 64, 8108-8121.
23. Ley, S. V.; Baeschlin, D. K.; Dixon, D. J.; Foster, A. C.; Ince, S. J.; Priepke, H. W. M.; Reynolds, D. J. Chem. Rev. 2001, 101, 53-80.
24. Piers, E.; Lemieux, R. Organometallics 1995, 14, 5011-5012.
25. It has to be pointed out that use of pyridine or 2,6-lutidine resulted in a 1:1 mixture of C-7/8 O-acyl regioisomers.
26. Corey, E. J.; Gross, A. Tetrahedron Lett. 1984, 25, 495-498.
27. Selected NOE data for 10. (Chemical Equation Presented)
28. Cadogan, J. I. G. Orgnanophosphorus Reagents in Organic Synthesis; Academic Press: New York, 1979.
29. Mitsunobu, O. Synthesis 1981, 1, 1-28.
30. Grubbs, R. H.; Schwab, B.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
31. (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
32. (b) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973-9976.
33. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
34. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.