Total synthesis of (-)-serotobenine

Journal of the American Chemical Society

Volumn 130, Issue 50, 2008, Pages 16854-16855

  Koizumi, Yasuaki ^a   Kobayashi, Hideki ^b   Wakimoto, Toshiyuki ^a   Furuta, Takumi ^a,c   Fukuyama, Tohru ^b   Kan, Toshiyuki ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURANS; INDOLES; ISOMERISM; MOLECULAR STRUCTURE;

EID: 58049213988     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807676v     Document Type: Article

References (23)

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8. The selectivity was depended on a stability of the intermediate. The similar reaction was reported; see: Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1984, 1333.
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11. Kan, T.; Inoue, T.; Kawamoto, Y.; Yonehara, M.; Fukuyama, T. Synlett 2006, 1583.
12. (a) Davies, H. M. L.; Hansen, T. J. Am. Chem. Soc. 1997, 119, 9075.
13. (b) Davies, H. M. L.; Antoulinakis, E. G. J. Organomet. Chem. 2001, 617, 47.
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15. (d) Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063.
16. The detailed selectivity by employment with other catalysts was described in supporting information.
17. In the total synthesis of ephedradine-A, a similar dihydrobenzofuran ring was constructed via a lactamide auxiliary; see ref 3b. As expected, changing the corresponding methyl group to a bulky phenyl derivative increased the selectivity.
18. Tilley, J. W.; Clader, J. W.; Zawoiski, S.; Wirkus, M.; LeMahieu, R. A.; O'Donnell, M.; Crowley, H.; Welton, A. F. J. Med. Chem. 1989, 32, 1814.
19. For review, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
20. Bajwa, J. S.; Chen, G.-P.; Prasad, K.; Repič, O.; Blacklock, T. J. Tetrahedron Lett. 2006, 47, 6425.
21. Detailed data are described in the Supporting Information.
22. Aldous, D. J.; Dalençon, A. J.; Steel, P. G. J. Org. Chem. 2003, 68, 9159.
23. During the course of isolating decursivine (2), Professor Fong detected serotobenine (1) from the same natural source; see ref 2a. Although they did not verify the optical purity of 1, biosynthesis of 2 would be derived from 1.