Asymmetric total synthesis of glycinoeclepin A: Generation of a novel bridgehead anion species

Chemistry Letters

Volumn 39, Issue 8, 2010, Pages 835-837

  Shiina, Yasuhiro ^a   Tomata, Yoshihide ^a   Miyashita, Masaaki ^b   Tanino, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KOGAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77954810962     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2010.835     Document Type: Review

References (23)

1. M. Tsutsumi, K. Sakurai, Jpn. J. Appl. Entomol. Zool. 1966, 10, 129.
2. a) T. Masamune, M. Anetai, M. Takasugi, N. Katsui, Nature 1982, 297, 495.
3. b) A. Fukuzawa, A. Furusaki, M. Ikura, T. Masamune, L. D. Hall, V. Rajanayagam, J. Chem. Soc. Chem. Commun. 1985, 748.
4. a) A. Murai, N. Tanimoto, N. Sakamoto, T. Masamune, J. Am. Chem. Soc. 1988, 110, 1985.
5. b) K. Mori, H. Watanabe, Pure Appl, Chem. 1989, 61, 543.
6. c) E. J. Corey, I. N. Houpis, J. Am. Chem. Soc 1990, 112, 8997.
7. d) H, Watanabe, K, Mori, J. Chem. Soc, Perkin Trans. 1 1991, 2919.
8. K. Tanino, Y. Tomata, Y. Shiina, M. Miyashita, Eur. J. Org. Chem. 2006, 328.
9. J.-P. Uttaro, G. Audran, H. Monti, J. Org. Chem. 2005, 70, 3484, and references cited therein
10. Since nitrile 2b proved to be unsuitable for large scale synthesis due to its high volatility, nitrile 8 was used for the cyclopentene annulation method instead of 2b. Nitrile 8 was prepared from glycerol monobenzyl ether as shown bellow. (Chemical Equation)
11. A similar transformation for the stereoselective synthesis of a steroid was reported: N. Miyaura, T. Ishiyama, H. Sasaki, M. Ishikawa, M. Satoh, A. Suzuki, J. Am. Chem. Soc 1989, 111, 314.
12. For a review: D. L. Hughes, Org. React. 1992, 42, 335.
13. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
14. H. Bredereck, G. Simchen, S. Rebsdat, W. Kantlehner, P. Horn, R. Wahl, H. Hoffman, P. Grieshaber, Chem. Ber. 1968, 101, 41;
15. See also: B. Trost, M. Preckel, J. Am. Chem. Soc. 1973, 95, 7862.
16. Y. Yoshida, Y. Sakakura, N. Aso, S. Okada, Y. Tanabe, Tetrahedron 1999, 55, 2183.
17. Y. Lu, G. Barth, K. Kieslich, P. D. Strong, W. L. Duax, C. Djerassi, J. Org. Chem. 1983, 48, 4549.
18. H. C. Brown, J. Chandrasekharan, P. V. Ramachandran, J. Am. Chem. Soc. 1988, 110, 1539.
19. Alcohol 22 was converted to the corresponding (R)- and (S)MTPA esters, which enabled us to estimate the enantiomeric purity and the absolute configuration of 22 by Kusumi's protocol: I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem, Soc. 1991, 113, 4092.
20. The minor diastereomer of iodo ketone 23 remained unchanged, suggesting that the major isomer of 23 has a trans relationship of the hydroxy and iodo groups.
21. E. J. Corey, H. L. Pearce, J. Am. Chem. Soc. 1979, 101, 5841.
22. C. J. Hayes, N. S. Simpkins, D. T. Kirk, L. Mitchell, J. Baudoux, A. J. Blake, C. Wilson, J. Am. Chem. Soc. 2009, 131, 8196, and references cited therein.
23. Since it was difficult to separate the adduct from hydrazone 25, it was converted to the corresponding silyl ether 27.