Construction of the quaternary C-7 centre of akuammiline alkaloids. Synthesis of 3,4-secoakuammilan derivatives

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6611-6614

  Bennasar, M Lluïsa ^a   Zulaica, Ester ^a   Ramírez, Antonio ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARBAZOLE DERIVATIVE; CATHAFOLINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030565532     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01412-8     Document Type: Article

References (22)

1. (a) Joule, J. A. In Indoles, The Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocydic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, pp 244-264.
2. (b) Alvarez, M.; Joule, J. In Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocydic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Vol. 25, Supplement to Part 4, pp 248-259.
3. Kisakürek, M. V.; Leeuwenberg, A. J. M.; Hesse, M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1983; Vol. 1, Chapter 5.
4. The biogenetic numbering is used throughout this paper: Le Men, J.; Taylor, W. I. Experientia 1965, 27, 508-510.
5. Koike, T.; Takayama, H.; Sakai, S. Chem. Pharm. Bull. 1991, 39, 1677-1681.
6. Bennasar, M.-L.; Zulaica, E.; Ramírez, A.; Bosch, J. J. Org. Chem. 1996, 61, 1239-1251.
7. For the construction of a tetracyclic ABCE substructure of echitamine alkaloids, see: Levy, J.; Sapi, J.; Laronze, J.-Y.; Royer, D.; Toupet, L. Synlett 1992, 601-602.
8. Jacquier, M. J.; Vercauteren, J.; Massiot, G.; Le Men-Olivier, L.; Pusset, J; Sévenet, T. Phytochemistry 1982, 21, 2973-2977.
9. Bennasar, M.-L.; Zulaica, E.; Ramírez, A.; Bosch, J. Heterocyles 1996, 43, in press.
10. (a) De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157-405.
11. (b) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 6, Chapter 4.7.
12. Kennedy, M.; McKervey, M. A. Ibid, Comprehensive Organic Synthesis Vol 7, Chapter 2.4.
13. 10c alkaloids: (a) Gallagher, T.; Magnus, P.; Huffman, J. C. J. Am. Chem. Soc. 1983, 705, 4750-4757.
14. (b) Amat, M.; Bosch, J. J. Org. Chem. 1992, 57, 5792-5796.
15. Catena, J. L.; Valls, N.; Bosch, J.; Bonjoch, J. Tetrahedron Lett. 1994, 35, 4433-4436.
16. Calverley, M.-J. J. Chem. Res. (M) 1983, 1848-1890.
17. 2Ph), 51.8 (OMe), 105.9 (C-7), 108.7 (C-12), 117.4 (C-9), 119.3 (C-10), 120.3, 121.0 (C-11, C-19), 125.5 (C-8), 133.5 (C-20), 135.4 (C-2), 136.9 (C-13), 169.7, 174.7 (CO).
18. All yields are from material purified by column chromatography. All new compounds gave satisfactory spectral, analytical and/or HMRS data.
19. 2Ph), 51.9 (OMe), 61.2 (C-6), 105.9 (C-7), 108.9 (C-12), 117.5 (C-9), 119.4 (C-10), 121.1, 124.5 (C-11, C-19), 125.5 (C-8), 133.0 (C-20), 135.4 (C-2), 136.6 (C-13), 165.4, 174.6 (CO).
20. 2Ph), 49.0 (C-16), 51.5 (C-21), 51.6 (OMe), 52.5 (C-7), 62.3 (C-6), 69.2 (C-2), 106.3 (C-12), 117.0 (C-10), 127.3-130.5 (complex signal), 131.5 (C-8), 135.5 (C-20), 153.0 (C-13), 170.4, 174.7 (CO).
21. 2Ph), 47.5 (C-7), 50.3 (C-6), 51.3 (C-16), 51.6 (OMe), 52.6 (C-21), 65.4 (C-2), 106.8 (C-12), 116.5 (C-10), 123.1 (C-9), 126.9 (C-19), 127.4 (C-11), 128.4, 128.6 (Ph), 134.7 (C-8), 136.4 (Ph), 137.0 (C-20), 151.4 (C-13), 170.4, 174.9 (CO).
22. Massiot, G.; Lavaud, C.; Vercauteren, J.; Le Men-Olivier, L.; Levy, J.; Guilhem, J.; Pascard, C. Helv. Chim. Acta 1983, 66, 2414-2430.