Enantioselective syntheses of the indole alkaloid (+)-R-decarbomethoxytetrahydrosecodine and its enantiomer

Tetrahedron Asymmetry

Volumn 7, Issue 11, 1996, Pages 3091-3094

  Amat, Mercedes ^a   Pshenichnyi, Grigorii ^a   Bosch, Joan ^a   Molins, Elies ^b   Miravitlles, Carles ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DECARBOMETHOXYTETRAHYDROSECODINE; INDOLE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0030575797     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00405-3     Document Type: Article

References (27)

1. 1. Atta-ur-Rahman; Basha, A. Biosynthesis of Indole Alkaloids; Clarendon Press: Oxford, 1983; p 98.
2. 2. Crooks, P. A.; Robinson, B.; Smith, G. F. J. Chem. Soc., Chem. Commun. 1968, 1210.
3. 3. For further isolations from other species, see: a) Robert, G. M. T.; Ahond, A.; Poupat, C.; Potier, P.; Jollès, C.; Jousselin, A.; Jacquemin, H. J. Nat. Prod. 1983, 46, 694.
4. b) Atta-ur-Rahman; Zaman, K.; Perveen, S.; Habib-ur-Rehman; Muzaffar, A.; Choudhary, M. I.; Pervin, A. Phytochemistry 1991, 30, 1285.
5. c) Mroue, M. A.; Ghuman, M. A.; Alam, M. Phytochemistry 1993, 33, 217.
6. 4. Palmisano, G.; Santagostino, M.; Riva, S.; Sisti, M. Tetrahedron: Asymmetry 1995, 6, 1229.
7. 5. For a synthesis of (±)-1, see reference 2.
8. 6. Sakagami, H.; Samizu, K.; Kamikubo, T.; Ogasawara, K. Synlett 1996, 163.
9. 7. a) Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. J. Org. Chem. 1994, 59, 10.
10. b) Amat, M.; Sathyanarayana, S.; Hadida, S.; Bosch, J. Heterocycles 1996, 43, 000.
11. 8. a) Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223.
12. b) Amat, M.; Llor, N.; Hidalgo, J.; Hernández, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977.
13. c) Amat, M.; Hidalgo, J.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 1845.
14. d) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molins, E.; Miravitlles, C. Tetrahedron: Asymmetry 1996, 7, 2501.
15. 1H COSY and HETCOR spectra were used to assign individual NMR signals.
16. 10. There are no studies about 2-alkyl-3-lithioindoles. However, see: Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. For leading references concerning 3-lithioindoles, see reference 7a.
17. 2), 28.1 (C-8), 42.8 (C-6), 58.2 (C-3), 72.7 (C-2), 88.8 (C-8a), 125.7 (C-o), 127.4 (C-p), 128.7 (C-m), 139.7 (C-ipso), 171.7 (C-5).
18. 8b
19. b) Micouin, L.; Varea, T.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2529.
20. 2), 29.4 (C-4), 36.5 (C-3), 45.4 (C-6), 49.9 (C-2).
21. 3) δ 0.85 (qd, J= 12.0, 5.0 Hz, 1H, H-15ax), 0.90 (t, J= 7.5 Hz, 3H, H-18), 1.24 (m, 2H, H-19), 1.27 (t, J= 7.5 Hz, 3H, H-17), 1.54 (m, 1H, H-20ax), 1.62-1.74 (m, 3H, H-21ax, 2H-14), 1.80 (dm, J= 12.0 Hz, 1H, H-15eq), 1.96 (td, J= 11.0, 2.5 Hz, 1H, H-3ax), 2.56 (m, 2H, H-5), 2.75 (q, J= 7.5 Hz, 2H, H-16), 2.92 (m, 2H, H-6), 3.02-3.10 (m, 2H, H-3eq, H-21eq), 7.05 (td, J= 7.0, 1.0 Hz, 1H, H-10), 7.09 (td, J= 7.0, 1.0 Hz, 1H, H-11), 7.26 (dm, J= 7.0 Hz, 1H, H-12), 7.51 (dm, J= 7.0 Hz, 1H, H-9), 7.79 (br s, 1H, NH).
22. 6
23. -3 Complete data have been deposited at the Cambridge Crystallographic Data Centre.
24. 18. a) Günther, A. Chem. Ber. 1898, 31, 2134.
25. b) Ripperger, H; Schreiber, K.; Sych, F.-J. J. Prakt. Chem. 1970, 312, 471.
26. c) Sakai, S.; Aimi, N.; Kato, K.; Ido, H.; Masuda, K.; Watanabe, Y.; Haginiwa, J. Yakugaku Zasshi 1975, 95, 1152.
27. d) Morlacchi, F.; Losacco, V.; Tortorella, V. J. Heteracyclic Chem. 1979, 16, 297.