Stereoselective synthesis of cis-1,3-dimethyltetrahydroisoquinolines: Formal synthesis of naphthylisoquinoline alkaloids

European Journal of Organic Chemistry

Volumn , Issue 28, 2012, Pages 5491-5497

  Amat, Mercedes ^a   Subrizi, Fabiana ^a   Elias, Viviane ^a   Llor, Núria ^a   Molins, Elies ^b   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Alkaloids; Asymmetric synthesis; Lactams; Nitrogen heterocycles; Total synthesis

Indexed keywords

EID: 84866490971     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201200798     Document Type: Article

References (32)

1. G. Bringmann, The Alkaloids (Ed.:, A. Brossi), Academic Press, New York, 1986, vol. 29, pp. 141-184.
2. G. Bringmann, F. Pokorny, The Alkaloids (Ed.:, G. Cordell), Academic Press, New York, 1995, vol. 46, pp. 127-271.
3. G. Bringmann, A. Irmer, D. Feineis, T. A. M. Gulder, H.-P. Fiedler, Phytochemistry 2009, 70, 1776-1786.
4. Y. F. Hallock, K. P. Manfredi, J. W. Blunt, J. H. Cardellina II, M. Schäffer, K.-P. Gulden, G. Bringmann, A. Y. Lee, J. Clardy, G. François, M. R. Boyd, J. Org. Chem. 1994, 59, 6349-6355.
5. M. A. Rizzacasa, M. V. Sargent, B. W. Skelton, A. H. White, Aust. J. Chem. 1990, 43, 79-86 (racemic series)
6. G. Bringmann, R. Weirich, H. Reuscher, J. R. Jansen, L. Kinzinger, T. Ortmann, Liebigs Ann. Chem. 1993, 877-888.
7. T. R. Hoye, M. Chen, Tetrahedron Lett. 1996, 37, 3099-3100.
8. T. R. Hoye, M. Chen, B. Hoang, L. Mi, O. P. Priest, J. Org. Chem. 1999, 64, 7184-7201.
9. F. A. Davis, P. K. Mohanty, D. M. Burns, Y. W. Andemichael, Org. Lett. 2000, 2, 3901-3903.
10. C. J. Bungard, J. C. Morris, J. Org. Chem. 2006, 71, 7354-7363. See also
11. G. L. Grunewald, T. M. Caldwell, Q. Li, K. R. Criscione, Bioorg. Med. Chem. 1999, 7, 869-880 for the synthesis of cis-1,3-disubstituted tetrahydroisoquinolines by 1,3-cis-selective Pictet-Spengler reactions, see
12. Y.-C. Wu, M. Liron, J. Zhu, J. Am. Chem. Soc. 2008, 130, 7148-7152, and references therein.
13. For a similar cyclocondensation reaction, see:, M. J. Munchhof, A. I. Meyers, J. Org. Chem. 1995, 60, 7086-7087 for reviews on the use of phenylglycinol-derived lactams as enantiomeric scaffolds in alkaloid synthesis, see
14. G. P. Brengel, A. I. Meyers, Chem. Commun. 1997, 1-8.
15. M. D. Groaning, A. I. Meyers, Tetrahedron 2000, 56, 9843-9873.
16. C. Escolano, M. Amat, J. Bosch, Chem. Eur. J. 2006, 12, 8198-8207.
17. M. Amat, M. Pérez, J. Bosch, Synlett 2011, 143-160.
18. M. Amat, N. Llor, R. Griera, M. Pérez, J. Bosch, Nat. Prod. Commun. 2011, 6, 515-526.
19. M. Amat, M. Pérez, J. Bosch, Chem. Eur. J. 2011, 17, 7724-7732.
20. Prepared as reported in:, A. Kamal, A. Sandhu, Tetrahedron Lett. 1963, 4, 611-612.
21. For an early biomimetic synthesis, see:, G. Bringmann, J. R. Jansen, Heterocycles 1986, 24, 2407-2410.
22. CCDC-870255 (for 2) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
23. For the stereochemical outcome of related Red-Al reductions, see:, M. Amat, O. Bassas, N. Llor, M. Cantó, M. Pérez, E. Molins, J. Bosch, Chem. Eur. J. 2006, 12, 7872-7881, and references therein.
24. M. C. Couturier, J. L. Tucker, B. M. Andersen, P. Dubé, J. T. Negri, Org. Lett. 2001, 3, 465-467.
25. For the generation of vinyl triflates from 2-piperidone derivatives, see:, C. J. Foti, D. L. Comins, J. Org. Chem. 1995, 60, 2656-2657.
26. D. L. Comins, A. Dehghani, Tetrahedron Lett. 1992, 33, 6299-6302.
27. 3SiH/TFA (room temp., 3 h) was not satisfactory from the stereochemical standpoint because it led to mixtures of cis/trans isomers (with Boc deprotection from 8b). This was initially attributed to a low facial selectivity in the generation of the C-3 stereocenter. However, epimerization at C-1 can also occur in the presence of TFA (see below in the main text). The isolation (33 %) of the ring-opening product 12 in the reduction of 8c confirms this interpretation; for the stereoselective reduction of 1,2- dihydroisoquinolines to cis-1,3-substituted tetrahydroisoquinolines under ionic hydrogenation conditions, see:, P. Magnus, K. S. Matthews, V. Lynch, Org. Lett. 2003, 5, 2181-2184.
28. [4d]
29. M. M. Bastiaans, J. L. van der Baan, H. C. Ottenheijm, J. Org. Chem. 1997, 62, 3880-3889.
30. P. Chau, I. R. Czuba, M. A. Rizzacasa, J. Org. Chem. 1996, 61, 7101-7105.
31. G. Bringmann, S. Rüdenauer, T. Bruhn, L. Benson, R. Brun, Tetrahedron 2008, 64, 5563-5568.
32. M. Amat, V. Elias, N. Llor, F. Subrizi, E. Molins, J. Bosch, Eur. J. Org. Chem. 2010, 4017-4026.