Synthesis of N-acetyl-1,3-dimethyltetrahydroisoquinolines by intramolecular amidomercuration: Stereochemical aspects

Synlett

Volumn , Issue 12, 2002, Pages 2065-2067

  De Koning, C B ^a   Michael, Joseph P ^a   Van Otterlo, Willem A L ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

Amidomercuration; Cyclization; Isoquinoline; Mitsunobu; Rotamers

Indexed keywords

AMIDE; MERCURY DERIVATIVE; MESYLIC ACID DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CIS TRANS ISOMERISM; CYCLIZATION; HIGH TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036456171     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35594     Document Type: Article

References (44)

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2. (b) For a recent example see: Iwasa, K.; Moriyasu, M.; Tachibana, Y.; Kim, H.-S.; Wataya, Y.; Wiegrebe W.; Bastow, K. F.; Cosentino, L. M.; Kozuka, M.; Lee, K.-H. Bioorg. Med. Chem. 2001, 9, 2871.
3. Bringmann G.; Pokorny, F. In The Alkaioids. Chemistry and Pharmacology, Vol. 46; Cordell, G. A., Ed.; Academic Press: San Diego, 1995, Chap. 4, 127-271.
4. Some recent representative syntheses and references therein: (a) Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090. (b) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965. (c) Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. J. Org. Chem. 1999, 64, 7184. (d) Lipshutz, B. H.; Keith, J. M. Angew Chem. Int. Ed. 1999, 38, 3530. (e) Rizzacasa, M. A.; Sargent, M. V. J. Chem. Soc., Perkin Trans. I 1991, 2773.
5. Some recent representative syntheses and references therein: (a) Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090. (b) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965. (c) Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. J. Org. Chem. 1999, 64, 7184. (d) Lipshutz, B. H.; Keith, J. M. Angew Chem. Int. Ed. 1999, 38, 3530. (e) Rizzacasa, M. A.; Sargent, M. V. J. Chem. Soc., Perkin Trans. I 1991, 2773.
6. Some recent representative syntheses and references therein: (a) Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090. (b) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965. (c) Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. J. Org. Chem. 1999, 64, 7184. (d) Lipshutz, B. H.; Keith, J. M. Angew Chem. Int. Ed. 1999, 38, 3530. (e) Rizzacasa, M. A.; Sargent, M. V. J. Chem. Soc., Perkin Trans. I 1991, 2773.
7. Some recent representative syntheses and references therein: (a) Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090. (b) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965. (c) Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. J. Org. Chem. 1999, 64, 7184. (d) Lipshutz, B. H.; Keith, J. M. Angew Chem. Int. Ed. 1999, 38, 3530. (e) Rizzacasa, M. A.; Sargent, M. V. J. Chem. Soc., Perkin Trans. I 1991, 2773.
8. Some recent representative syntheses and references therein: (a) Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090. (b) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965. (c) Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. J. Org. Chem. 1999, 64, 7184. (d) Lipshutz, B. H.; Keith, J. M. Angew Chem. Int. Ed. 1999, 38, 3530. (e) Rizzacasa, M. A.; Sargent, M. V. J. Chem. Soc., Perkin Trans. I 1991, 2773.
9. Some recent examples from groups working in the area: (a) Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731. (b) Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497. (c) Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523. (d) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. (e) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1. (f) Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687. (g) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.-R.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371. (h) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037. (i) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. J. Chem. Soc., Perkin Trans. I 2000, 799.
10. Some recent examples from groups working in the area: (a) Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731. (b) Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497. (c) Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523. (d) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. (e) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1. (f) Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687. (g) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.-R.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371. (h) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037. (i) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. J. Chem. Soc., Perkin Trans. I 2000, 799.
11. Some recent examples from groups working in the area: (a) Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731. (b) Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497. (c) Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523. (d) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. (e) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1. (f) Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687. (g) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.-R.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371. (h) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037. (i) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. J. Chem. Soc., Perkin Trans. I 2000, 799.
12. Some recent examples from groups working in the area: (a) Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731. (b) Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497. (c) Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523. (d) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. (e) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1. (f) Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687. (g) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.-R.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371. (h) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037. (i) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. J. Chem. Soc., Perkin Trans. I 2000, 799.
13. Some recent examples from groups working in the area: (a) Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731. (b) Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497. (c) Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523. (d) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. (e) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1. (f) Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687. (g) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.-R.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371. (h) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037. (i) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. J. Chem. Soc., Perkin Trans. I 2000, 799.
14. Some recent examples from groups working in the area: (a) Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731. (b) Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497. (c) Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523. (d) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. (e) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1. (f) Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687. (g) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.-R.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371. (h) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037. (i) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. J. Chem. Soc., Perkin Trans. I 2000, 799.
15. Some recent examples from groups working in the area: (a) Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731. (b) Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497. (c) Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523. (d) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. (e) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1. (f) Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687. (g) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.-R.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371. (h) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037. (i) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. J. Chem. Soc., Perkin Trans. I 2000, 799.
16. Some recent examples from groups working in the area: (a) Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731. (b) Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497. (c) Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523. (d) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. (e) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1. (f) Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687. (g) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.-R.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371. (h) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037. (i) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. J. Chem. Soc., Perkin Trans. I 2000, 799.
17. Some recent examples from groups working in the area: (a) Bringmann, G.; Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731. (b) Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497. (c) Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523. (d) Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331. (e) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1. (f) Zhang, H.; Zembower, D. E.; Chen, Z. Bioorg. Med. Chem. Lett. 1997, 7, 2687. (g) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.-R.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371. (h) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. Tetrahedron Lett. 1999, 40, 3037. (i) de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L. J. Chem. Soc., Perkin Trans. I 2000, 799.
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23. This work is taken from the PhD thesis of W. A. L. van Otterlo, University of the Witwatersrand, 1999.
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38. 4OH, 66:33:1) afforded the 1,3-trans-dimethyl cyclized product 3 (0.11 g, 56%) as a light yellow oil.
39. 13C NMR spectrum also showed two characteristic sets of resonances: at δ = 49.1 and 46.7 (C-1) ppm, δ = 46.3 and 44.4 (C-3) ppm and δ = 28.6 and 27.8 (C-4) ppm.
40. Example of rotational isomers in tetrahydroisoquinolines due to N-acetyl and N-formyl substituents: Bringmann, G.; Holenz, J.; Wiesen, B.: Nugroho, B. W.; Proksch, P. J. Nat. Prod. 1997, 60, 342.
41. de Koning, C. B.; Michael, J. P.; van Otterlo, W. A. L., unpublished results.
42. For isomer 3, the C-1 methyl substituent showed an NOE with the H-4 pseudo-axial proton, indicating that the C-1 methyl substituent must be pseudo-axial. For the cis-isomer 9 the same NOE was seen, as well as an NOE between the 1-methyl and 3-methyl substituents, thereby fixing the cis-arrangement. Therefore in isomer 3 the C-1 methyl and C-3 methyl groups must be trans.
43. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
44. 4OH, 66:33:1) afforded an equimolar mixture of the 1,3-trans-dimethyl product 3, its 1,3-cis-dimethyl isomer 9 (0.027 g, 85%) as rotamers about the N-Ac bond.