Total synthesis and structural revision of sekothrixide

Organic Letters

Volumn 16, Issue 11, 2014, Pages 2794-2797

  Terayama, Naoki ^a   Yasui, Eiko ^a   Mizukami, Megumi ^b   Miyashita, Masaaki ^a   Nagumo, Shinji ^a  

^a KOGAKUIN UNIVERSITY   (Japan)

^b HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; LACTONE; MACROLIDE; SEKOTHRIXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

HETEROCYCLIC COMPOUNDS; LACTONES; MACROLIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84902076138     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5006856     Document Type: Article

References (39)

1. Smith, C. D.; Zilfou, J. T.; Stratmann, K.; Patterson, G. M. L.; Moore, R. E. Mol. Pharmacol. 1995, 47, 241-247
2. Zhang, X.; Smith, C. D. Mol. Pharmacol. 1996, 49, 288-294
3. Gottesman, M. M. Annu. Rev. Med. 2002, 53, 615-627
4. Kim, Y. J.; Furihata, K.; Shimazu, A.; Furihata, K.; Seto, H. J. Antibiot. 1991, 44, 1280-1282
5. 1H NMR spectrum of sekothrixide can be seen in this thesis.
6. Fujita, K.; Fujiwara, M.; Yamasaki, C.; Matsuura, T.; Furihata, K.; Seto, H. Stereochemistry Structure Determination Method Used by Computer. Proc. 38th Symp. Chem. Nat. Prod. Sendai, Japan, Oct 14-16, 1996; pp 379-384.
7. Celmer, W. D. J. Am. Chem. Soc. 1965, 87, 1797-1799
8. Celmer, W. D. J. Am. Chem. Soc. 1965, 87, 1799-1801
9. Celmer, W. D. J. Am. Chem. Soc. 1965, 87, 1801-1802
10. Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Weinheim, 2003; Vol. 2.
11. Gradillas, A.; Pérez-Castells, J. Angew. Chem., Int. Ed. 2006, 45, 6086-6101
12. Majumdar, K. C.; Rahaman, H.; Roy, B. Curr. Org. Chem. 2007, 11, 1339-1365
13. Diederich, F.; Stang, P. J.; Tykwinski, R. R. Modern Supramolecular Chemistry: Strategies for Macrocycle Synthesis; Wiley-VCH: Weinheim, 2008; Chapter II, pp 29-67.
14. Cossy, J.; Arseniyadis, S.; Meyer, C. Metathesis in Natural Product Synthesis; Wiley-VCH: Weinheim, 2010.
15. Kumar, V. P.; Chandrasekhar, S. Org. Lett. 2013, 15, 3610-3613
16. Hwang, M.-H.; Han, S.-J.; Lee, D.-H. Org. Lett. 2013, 15, 3318-3321
17. Volchkov, I.; Lee, D. J. Am. Chem. Soc. 2013, 135, 5324-5327
18. Gao, X.; Woo, S. K.; Krische, M. J. Am. Chem. Soc. 2013, 135, 4223-4226
19. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739
20. Fujita, K.; Mori, K. Eur. J. Org. Chem. 2001, 493-502
21. Tanino, K.; Shimizu, T.; Kuwahara, M.; Kuwajima, I. J. Org. Chem. 1998, 63, 2422-2423
22. Iwata, Y.; Tanino, K.; Miyashita, M. Org. Lett. 2005, 7, 2341-2344
23. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719-2722
24. Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 4871-4874
25. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976
26. Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans. 1 1983, 1315-1318
27. Sasaki, M.; Tanino, K.; Miyashita, M. J. Org. Chem. 2001, 66, 5388-5394
28. Sasaki, M.; Miyazawa, M.; Tanino, K.; Miyashita, M. Tetrahedron Lett. 1999, 40, 9267-9270
29. Liu, C.; Hashimoto, Y.; Kudo, K.; Saigo, K. Bull. Chem. Soc. Jpn. 1996, 69, 2095-2105
30. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553
31. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240
32. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096
33. Wrona, I. E.; Gozman, A.; Taldone, T.; Chiosis, G.; Panek, J. S. J. Org. Chem. 2010, 75, 2820-2835
34. Dias, L. C.; Melgar, G. Z.; Jardim, L. S. A. Tetrahedron Lett. 2005, 46, 4427-4431
35. 3)] as a precursor of ent-24.
36. Penning, T. D.; Djuric, S. W.; Haack, R. A.; Kalish, V. J.; Miyashiro, J. M.; Rowell, B. W.; Yu, S. S. Synth. Commun. 1990, 20, 307-312
37. Mukaiyama, T.; Matsui, S.; Kashiwagi, K. Chem. Lett. 1989, 18, 993-996
38. Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. J. Org. Chem. 2004, 69, 1822-1830
39. Stothers, J. B. Carbon-13 NMR Spectroscopy; Academic Press: New York, 1972; pp 389-506.