Concise syntheses of harmicine and a pyrrolidino-isoquinoline derivative using chiral 1-allyl adducts of β-carboline and isoquinoline as starting materials

Heterocycles

Volumn 58, Issue , 2002, Pages 115-118

  Itoh, Takashi ^a   Miyazaki, Michiko ^a   Nagata, Kazuhiro ^a   Yokoya, Masashi ^a   Nakamura, Shigeru ^a   Ohsawa, Akio ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,5,6,10B HEXAHYDROPYRROLO[2,1 A]ISOQUINOLINE; ALKALOID; BETA CARBOLINE; HARMICINE; ISOQUINOLINE; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0037159696     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-s(m)49     Document Type: Article

References (29)

1. This paper is dedicated to Professor A. I. Meyers on the occasion of his 70th birthday.
2. a) T. Itoh, K. Nagata, M. Miyazaki, and A. Ohsawa, Synlett, 1999, 1154.
3. b) T. Itoh, K. Nagata, M. Miyazaki, K. Kameoka, and A. Ohsawa, Tetrahedron, 2001, 57, 8827.
4. a) T. Itoh, Y. Matsuya, Y. Enomoto, K. Nagata, M. Miyazaki, and A. Ohsawa, Synlett, 1999, 1799.
5. b) Y. Matsuya, T. Itoh, Y. Enomoto, and A. Ohsawa, Heterocycles, 2000, 53, 2357.
6. c) T. Itoh, Y. Matsuya, Y. Enomoto, and A. Ohsawa, Tetrahedron, 2001, 57, 7277.
7. Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207, and references cited therein.
8. a) S. F. Martin, B. Benage, and J. E. Hunter, J. Am. Chem. Soc., 1988, 110, 5925.
9. b) S. F. Martin, B. Benage, L. S. Geraci, J. E. Hunter, and M. Mortimore, J. Am. Chem. Soc., 1991, 113, 6161.
10. c) R. Yamaguchi, T. Hamasaki, T. Sasaki, T. Ohta, K. Utimoto, S. Kozima, and H. Takaya, J. Org. Chem., 1993, 58, 1136.
11. d) V. B. Birman and V. H. Rawal, Tetrahedron Lett., 1998, 39, 7219.
12. e) V. B. Virman and V. H. Rawal, J. Org. Chem., 1998, 63, 9146.
13. a) B. A. Dadson, J. Harler-Mason, and G. H. Foster, J. Chem. Soc., Chem. Commun., 1968, 1233.
14. b) J. Harley-Mason and C. G. Tayler, J. Chem. Soc., Chem. Commun., 1970, 812.
15. c) G. C. Crawley and J. Harley-Mason, J. Chem. Soc., Chem. Commun., 1971, 685.
16. d) W. R. Ashcroft, S. J. Martinez, and J. A. Joule, Tetrahedron, 1981, 37, 3005.
17. T.-S. Kam and K.-M. Sim, Phytochemistry, 1998, 47, 145.
18. Modification of the reported method in ref. 2 raised the ee to 91% using an N-pyroglutamic acid derivative as a chiral auxiliary. The detailed procedure will be reported in a due course.
19. R. C. Bernotas and R. V. Cube, Tetrahedron Lett., 1991, 32, 161.
20. B. E. Maryanoff, D. F. McComsey, J. F. Gardocki, R. P. Shank, M. J. Costanzo, S. O. Nortey, C. R. Schneider, and P. E. Setler, J. Med. Chem., 1987, 30, 1433, and references cited therein.
21. a) Y. Tsuda, Y. Sakai, M. Kaneko, and Y. Ishiguro, Heterocycles, 1981, 15, 431.
22. b) W. N. Speckamp and H. Hiemstra, Tetrahedron, 1985, 41, 4367.
23. c) E. Lete, A. Egiarte, N. Sotomayor, T. Vicente, and M.-J. Villa, Synlett, 1993, 41.
24. a) B. E. Maryanoff and D. F. McComsey, J. Heterocycl. Chem., 1985, 22, 911.
25. b) B. E. Maryanoff, D. F. McComsey, H. R. Almond Jr., M. S. Mutter, G. W. Bemis, R. R. Whittle, and R. A. Olofson, J. Org. Chem., 1986, 51, 1341.
26. c) B. E. Maryanoff, D. F. McComsey, M. S. Mutter, K. L. Sorgi, and C. A. Maryanoff, Tetrahedron Lett., 1988, 29, 5073.
27. d) K. L. Sorgi, C. A. Maryanoff, D. F. McComsey, D. W. Graden, and B. E. Maryanoff, J. Am. Chem. Soc., 1990, 112, 3567.
28. Y. S. Lee, D. W. Kang, S. J. Lee, and H. Park, J. Org. Chem., 1995, 60, 7149.
29. Direct formation of 10 from 8 was also possible by elongation of the reaction time (6 h) to give a comparable yield of 62%.