Stereoselective total synthesis of the proposed structure of 2-epibotcinolide

Organic Letters

Volumn 8, Issue 23, 2006, Pages 5279-5282

  Shiina, Isamu ^a   Takasuna, Yu Ji ^a   Suzuki, Ryo Suke ^a   Oshiumi, Hiromi ^a   Komiyama, Yuri ^a   Hitomi, Seiichi ^a   Fukui, Hiroki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BOTCININ E; DECANOIC ACID DERIVATIVE; LACTONE; PYRONE DERIVATIVE;

ARTICLE; BOTRYTIS; CHEMICAL STRUCTURE; CYCLIZATION; METABOLISM; SYNTHESIS;

BOTRYTIS; CYCLIZATION; DECANOATES; LACTONES; MOLECULAR STRUCTURE; PYRONES;

EID: 33845261538     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062058+     Document Type: Article

References (35)

1. (a) Cutler, H. G.; Jacyno, J. M.; Harwood, J. S.; Dulik, D.; Goodrich, P. D.; Roberts, R. G. Biosci. Biotechnol. Biochem. 1993, 57, 1980-1982.
2. (b) Jacyno, J. M.; Harwood, J. S.; Cutler, H. G.; Dulik, D. M. Tetrahedron 1994, 50, 11585-11592.
3. Collado, I. G.; Aleu, J.; Hernandez-Galan, R.; Hanson, J. R. Photochemistry 1996, 42, 1621-1624.
4. (a) Cutler, H. G.; Parker, S. R.; Ross, S. A.; Crumley, F. G.; Schreiner, P. R. Biosci. Biotechnol. Biochem. 1996, 60, 656-658.
5. (b) Reino, J. L.; Hernández-Galán, R.; Durán- Patrón, R.; Collado, I. G. J. Phytopathology 2004, 152, 563-566.
6. (c) Reino, J. L.; Durán-Patrón, R. M.; Daoubi, M.; Collado, I. G.; Hernández-Galán, R. J. Org. Chem. 2006, 71, 562-565.
7. (a) Tani, H.; Koshino, H.; Sakuno, E.; Cutler, H. G.; Nakajima, H. J. Nat. Prod. 2006, 69, 722-725.
8. (b) Tani, H.; Koshino, H.; Sakuno, E.; Nakajima, H. J. Nat. Prod. 2005, 68, 1768-1772.
9. (a) Shiina, I.; Takasuna, Y.; Komiyama, Y. Abstracts of Papers, 85th National Meeting of the Chemical Society of Japan, Yokohama, 2005; Vol. 2, 1A142;
10. (b) Shiina, I.; Takasuna, Y.; Komiyama, Y.; Suzuki, R.; Oshiumi, H. Abstracts of Papers, 86th National Meeting of the Chemical Society of Japan, Chiba, 2006; Vol. 2, 4L429;
11. (c) Shiina, I.; Komiyama, Y.; Takasuna, Y.; Hitomi, S. Abstracts of Papers, 86th National Meeting of the Chemical Society of Japan, Chiba, 2006; Vol. 2, 4L430.
12. Just before submitting our paper, Chakraborty et al. reported the synthesis of the nine-membered lactone core of botcinolides based on their independent methodology. They described that their prepared nine-membered ring corresponds to the assumed structure of 2-epibotcinolide (1b); however, there is a misunderstanding that the nine-membered ring produced by Chakraborty is not a precursor of 2-epibotcinolide (1b) but one of the diastereomers of 1b originated at the C8 position. This means that Chakraborty reported the first synthesis of the lactone moiety of 2-epi-8-epibotcinolide. Carefully note the stereochemistry of the seco-acid (19, the number used in their paper): Chakraborty, T. K.; Goswami, R. K. Tetrahedron Lett. 2006, 47, 4917-4919.
13. (a) Shiina, I.; Ibuka, R.; Kubota, M. Chem. Lett. 2002, 286-287.
14. (b) Shiina, I.; Kubota, M.; Ibuka, R. Tetrahedron Lett. 2002, 43, 7535-7539.
15. (c) Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. J. Org. Chem. 2004, 69, 1822-1830.
16. (d) Shiina, I.; Oshiumi, H.; Hashizume, M.; Yamai, Y.; Ibuka, R. Tetrahedron Lett. 2004, 45, 543-547.
17. (e) Shiina, I. J. Synth. Org. Chem. Jpn. 2005, 62, 2-17.
18. (f) Shiina, I.; Hashizume, M.; Yamai, Y.; Oshiumi, H.; Shimazaki, T.; Takasuna, Y.; Ibuka, R. Chem. Eur. J. 2005, 11, 6601-6608.
19. (g) Shiina, I.; Hashizume, M. Tetrahedron 2006, 62, 7934-7939.
20. See also: (h) Shiina, I.; Kawakita, Y. Tetrahedron 2004, 60, 4729-4733.
21. (a) Mukaiyama, T.; Kobayashi, S.; Uchiro, H.; Shiina, I. Chem. Lett. 1990, 129-132.
22. (b) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252.
23. (c) Shiina, I. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004; Vol. 2, pp 105-165.
24. (a) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2003, 5, 3021-3024.
25. (b) Inoue, M.; Sasaki, T.; Hatano, S.; Hirama, M. Angew. Chem., Int. Ed. 2004, 43, 6500-6505.
26. (c) Inoue, M. Bull. Chem. Soc. Jpn. 2006, 79, 501-510.
27. (d) Dinh, M.-T.; BouzBouz, S.; Peglion, J.-L.; Cossy, J. Synlett 2005, 2851-2853.
28. (e) Morita, M.; Mase, N.; Yoda, H.; Takabe, K. Tetrahedron: Asymmetry 2005, 16, 3176-3182.
29. (f) Doi, T.; Iijima, Y.; Shin-ya, K.; Ganesan, A.; Takahashi, T. Tetrahedron Lett. 2006. 47, 1177-1180.
30. (g) Hosokawa, S.; Seki, M.; Fukuda, H.; Tatsuta, K. Tetrahedron Lett. 2006, 47, 2439-2442.
31. (h) Nicolaou, K. C.; Xu, H. Chem. Commun. 2006, 600-602.
32. Wu, Y.; Yang, Y.-Q. J. Org. Chem. 2006, 71, 4296-4301.
33. (j) Tsuchikawa, H.; Matsushita, N.; Matsumori, N.; Muraka, M.; Oishi, T. Tetrahedron Lett. 2006, 47, 6187-6191.
34. Fukuyama, T.; Lin, S.-C.; Li, L.-P. J. Am. Chem. Soc. 1990, 112, 7050-7051.
35. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.