Heck cyclization strategy for preparation of erythrinan alkaloids: Asymmetric synthesis of unnatural (-)-erysotramidine from L -tartaric acid

Journal of Organic Chemistry

Volumn 80, Issue 3, 2015, Pages 1957-1963

  Mostowicz, Danuta ^a   Dygas, Mirosław ^a   Kałuza, Zbigniew ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN COMPOUNDS;

ALCOHOL ADDITIONS; ASYMMETRIC SYNTHESIS; HECK CYCLIZATION; HYDROGEN REDUCTION; L-TARTARIC ACIDS; N-ACYLIMINIUM CYCLIZATION; STEREOSELECTIVE REACTIONS; SYNTHESIS FEATURES;

CYCLIZATION;

10,11 DIMETHOXY 2 [[(TRIISOPROPYLSILYL)OXY]METHYL] 3A,4,7,8 TETRAHYDRO 1H FURO[3',2':2,3]PYRROLO[2,1 A]ISOQUINOLIN 5(2H) ONE; 10B [2 HYDROXY 3 [(TRIISOPROPYLSILYL)OXY]PROPYL] 8,9 DIMETHOXY 5,6 DIHYDROPYRROLO[2,1 A]ISOQUINOLIN 3(10BH) ONE; 10B [4 IODO 2 [(TRIETHYLSILYL)OXY]BUT 3 EN 1 YL] 8,9 DIMETHOXY 5,6 DIHYDROPYRROLO[2,1 A]ISOQUINOLIN 3 (10BH) ONE; 11,12 DIMETHOXY 2 [(TRIETHYLSILYL)OXY] 8,9 DIHYDRO 1H INDOLO[7A,1A]ISOQUINOLIN 6(2H) ONE; 11,12 DIMETHOXY 8,9 DIHYDRO 1H INDOLO[7A,1A]ISOQUINOLINE 2,6 DIONE; 2 (2 IODOVINYL) 10,11 DIMETHOXY 3A,4,7,8 TETRAHYDRO 1H FURO[3',2':2,3]PYRROLO[2,1 A]ISOQUINOLIN 5(2H) ONE; 2 HYDROXY 11,12 DIMETHOXY 8,9 DIHYDRO 1H INDOLO[7A,1A]ISOQUINOLIN 6(2H) ONE; 4 HYDROXY 10,11 DIMETHOXY 2 [[(TRIISOPROPYLSILYL)OXY]METHYL] 3A,4,7,8 TETRAHYDRO 1H FURO[3',2':2,3]PYRROLO[2,1 A]ISOQUINOLIN 5(2H) ONE; 4 HYDROXY 10,11 DIMETHOXY 2 [[(TRIISOPROPYLSILYL)OXY]METHYL] 7,8 DIHYDRO 3AH FURO[3',2':2,3]PYRROLO[2,1 A]ISOQUINOLIN 5(4H) ONE; 4 IODO 10,11 DIMETHOXY 2 [[(TRIISOPROPYLSILYL)OXY]METHYL] 3A,4,7,8 TETRAHYDRO 1H FURO[3',2':2,3]PYRROLO[2,1 A]ISOQUINOLIN 5(2H) ONE; 8,9 DIMETHOXY 3 OXO 10B [3 [(TRIISOPROPYLSIYL)OXY]PROP 1 YN 1 YL] 1,2,3,5,6,10B HEXAHYDROPYRROLO[2,1 A]ISOQUINOLINE 1,2 DIYL DIACETATE; ACETYLENE; ALCOHOL; ALKENE DERIVATIVE; ERYSOTRAMIDINE; ERYTHRINA ALKALOID; ETHER DERIVATIVE; FURAN DERIVATIVE; HYDROGEN; IMIDE; IODOOLEFIN; O [10,11 DIMETHOXY 5 OXO 2 [[(TRIISOPROPYLSILYL)OXY]METHYL] 2,3A,4,5,7,8 HEXAHYDRO 1H FURO[3',2':2,3]PYRROLO[2,1 A]ISOQUINOLIN 4 YL] 1H IMIDAZOLE 1 CARBOTHIOATE; SILVER; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYL ETHER; ALKALOID; ERYTHRININE; FUSED HETEROCYCLIC RINGS;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REDUCTION; RING OPENING; STEREOCHEMISTRY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR STRUCTURE; STEREOISOMERISM; TARTRATES;

EID: 84922738685     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5026157     Document Type: Article

References (56)

1. Hill, R. K. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, pp 483-515.
2. Dyke, S. F.; Quessy, S. N. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 18, pp 1-98.
3. Chawala, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 1, 371-373
4. Jackson, A. H. In Chemistry and Biology of Isoquinoline Alkaloids; Phillipson, J. D.; Margaret, M. F.; Zenk, M. H., Eds.; Springer: Berlin, Germany, 1985; pp 62-78.
5. Amer, M. A.; Shamma, M.; Freyer, A. J. J. Nat. Prod. 1991, 54, 329-363
6. Flausino, O., Jr.; Santos, L. A.; Verli, H.; Pereira, A. M.; Bolzani, V. S.; Nunes-de-Souza, R. L. J. Nat. Prod. 2007, 70, 48-53
7. For a comprehensive review of synthetic approaches to Erythrina alkaloids, see: Reimann, E. Synthesis Pathways to Erythrina Alkaloids and Erythrina Type Compounds. In Progress in the Chemistry of Organic Natural Products; Herz, W.; Falk, H.; Kirby, G. W., Eds.; Springer-Verlag: Wien, Austria, 2007; Vol. 88, pp 1-62, and references citied therein.
8. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144-1155
9. Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505-1511
10. Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T.; McClure, M. S.; Wang, Q. J. Org. Chem. 2002, 67, 5928-5937
11. Lee, H. I.; Cassidy, M. P.; Rashatasakhon, P.; Padwa, A. Org. Lett. 2003, 5, 5067-5070
12. El Bialy, S. A. A.; Braun, H.; Tietze, L. F. Angew. Chem., Int. Ed. 2004, 43, 5391-5393
13. Padwa, A.; Lee, H. I.; Rashatasakhon, P.; Rose, M. J. Org. Chem. 2004, 69, 8209-8218
14. Padwa, A.; Wang, Q. J. Org. Chem. 2006, 71, 7391-7402
15. Gao, S.; Tu, Y. Q.; Hu, X.; Wang, S.; Hua, R.; Jiang, Y.; Zhao, Y.; Fan, X.; Zhang, S. Org. Lett. 2006, 8, 2373-2376
16. Kim, G.; Kim, J. H.; Lee, K. Y. J. Org. Chem. 2006, 71, 2185-2187
17. Tuan, L. A.; Kim, G. Bull. Korean Chem. Soc. 2010, 31, 1801-1802
18. Kalaitzakis, D.; Montagnon, T.; Antonatou, E.; Vassilikogiannakis, G. Org. Lett. 2013, 15, 3714-3717
19. Heller, S. T.; Kiho, T.; Narayan, A. R. H.; Sarpong, R. Angew. Chem., Int. Ed. 2013, 52, 11129-11133
20. LHomme, Ch.; Ménard, M.-A.; Canesi, S. J. Org. Chem. 2014, 79, 8481-8484
21. Lee, J. Y.; Lee, Y. S.; Chung, B. Y.; Park, H. Tetrahedron 1997, 53, 2449-2458
22. Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803-7807
23. Allin, S. M.; Streetley, G. B.; Slater, M.; Jamesa, S. L.; Martin, W. P. Tetrahedron Lett. 2004, 45, 5493-5496
24. Yasui, Y.; Suzuki, K.; Matsumoto, T. Synlett 2004, 619-622
25. Blake, A. J.; Gill, C.; Greenhalgh, D. A.; Simpkins, N. S.; Zhang, F. Synthesis 2005, 3287-3292
26. Fukumoto, H.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Angew. Chem., Int. Ed. 2006, 45, 2731-2734
27. Zhang, F.; Simpkins, N. S.; Wilson, C. Tetrahedron Lett. 2007, 48, 5942-5947
28. Stanislawski, P. C.; Willis, A. C.; Banwell, M. G. Chem.-Asian J. 2007, 2, 1127-1136
29. Tietze, L. F.; Tölle, N.; Kratzert, D.; Stalke, D. Org. Lett. 2009, 11, 5230-5233
30. Zhang, F.; Simpkins, N. S.; Blake, A. J. Org. Biomol. Chem. 2009, 7, 1963-1979
31. Tsuda, Y.; Hosoi, S.; Katagiri, N.; Chikara, K.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087-2095
32. Mostowicz, D.; Wójcik, R.; Dołęga, G.; Kałuza, Z. Tetrahedron Lett. 2004, 45, 6011-6015
33. Kałuza, Z.; Mostowicz, D.; Dołęga, G.; Mroczko, K.; Wójcik, R. Tetrahedron 2006, 62, 943-953
34. Kałuza, Z.; Mostowicz, D.; Dołęga, G.; Wójcik, R. Tetrahedron 2008, 64, 2321-2328
35. Seth, P. P.; Totah, N. I. Org. Lett. 2000, 2, 2507-2509
36. Mejorado, L. H.; Hoarau, C.; Pettus, T. R. R. Org. Lett. 2004, 6, 1535-1538
37. Tinarelli, A.; Paolucci, C. J. Org. Chem. 2006, 71, 6630-6633
38. For a comprehensive review see: Brossi, A.; Pei, X.-F. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1998; Vol. 50, pp 109-139.
39. Farmer, R. L.; Biddle, M. M.; Nibbs, A. E.; Huang, X.; Bergan, R. C.; Scheidt, K. A. ACS Med. Chem. Lett. 2010, 1, 400-405
40. Kerr, D. J.; Flynn, B. L. Org. Lett. 2012, 14, 1740-1743
41. Kerr, D. J.; Miletic, M.; Manchala, N.; White, J. M.; Flynn, B. L. Org. Lett. 2013, 15, 4118-4121
42. Alibés, R.; Ballbé, M.; Busqué, F.; de March, P.; Elias, L.; Figueredo, M.; Font J. Org. Lett. 2004, 6, 1813-1816
43. Hua, D. H.; Zhao, H.; Battina, S. K.; Lou, K.; Jimenez, A. L.; Desper, J.; Perchellet, E. M.; Perchellet, J-P. H.; Chiang, P. K. Bioorg. Med. Chem. 2008, 16, 5232-5246
44. Bennasar, M.-L.; Solé, D.; Zulaica, E.; Alonso, S. Org. Lett. 2011, 13, 2042-2045
45. Bennasar, M.-L.; Solé, D.; Zulaica, E.; Alonso, S. Tetrahedron 2013, 69, 2534-2541
46. Obase, A.; Kageyama, A.; Manabe, Y.; Ozawa, T.; Araki, T.; Yokoe, H.; Kanematsu, M.; Yoshida, M.; Shishido, K. Org. Lett. 2013, 15, 3666-3669
47. Arimitsu, S.; Hammond, G. B. J. Org. Chem. 2007, 72, 8559-8561
48. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585
49. Lange, G. L.; Gottardo, C. Synth. Commun. 1990, 20, 1473-1479
50. Pedersen, P. J.; Andresen, T. L.; Clausen, M. H. Eur. J. Org. Chem. 2012, 6656-6661
51. Wullschleger, C. W.; Gertsch, J.; Altmann, K.-H. Chem. Eur. J. 2013, 19, 13105-13111
52. Chi, S.; Heathcock, C. H. Org. Lett. 1999, 1, 3-5
53. Davison, E. C.; Fox, M. E.; Holmes, A. B.; Roughley, S. D.; Smith, C. J.; Williams, G. M.; Davies, J. E.; Raithby, P. R.; Adams, J. P.; Forbes, I. T.; Press, N. J.; Thompsonc, M. J. J. Chem. Soc., Perkin Trans. 1 2002, 1494-1514
54. Goundry, W. R. F.; Baldwin, J. E.; Lee, V. Tetrahedron 2003, 59, 1719-1729
55. Li, P.; Li, J.; Arikan, F.; Ahlbrecht, W.; Dieckmann, M.; Menche, D. J. Org. Chem. 2010, 75, 2429-2444
56. Oliveira, J. M.; Freitas, J. C.; Comasseto, J. V.; Menezes, P. H. Tetrahedron 2011, 67, 3003-3009