5,6-Dihydropyrrolo[2,1-b]isoquinolines as scaffolds for synthesis of lamellarin analogues

Tetrahedron Letters

Volumn 46, Issue 12, 2005, Pages 2041-2044

  Olsen, Christian A ^a,b   Parera, Núria ^a,c   Albericio, Fernando ^a   Álvarez, Mercedes ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

Cross coupling reactions; Heterocycles; Marine alkaloids; Palladium

Indexed keywords

5,6 DIHYDROPYRROLO[2,1 B]ISOQUINOLINE; ALKALOID DERIVATIVE; ISOQUINOLINE DERIVATIVE; LAMELLARIN; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 14644424611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.145     Document Type: Article

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31. 3, 100 MHz) δ 162.0 (s, CO); 136.4 (s, C3); 131.9 (s, C10b); 128.6 (s, C10a); 128.6 (d, C10); 128.1 (d, C8); 127.7 (d, C9); 123.9 (d, C7); 122.0 (s, C6a); 118.6 (d, C2); 104.7 (d, C1); 51.3 (q, OMe); 42.4 (t, C5); 29.1 (t, C6)
32. N.B. Perry, L. Ettouati, M. Litaudon, J.W. Blunt, M.H.G. Munro, S. Parkin, and H. Hope Tetrahedron 50 1994 3987
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34. 2. The organic solution was washed with brine and water, dried and concentrated to give a crude material which was purified by column chromatography on silica gel
35. 3, 400 MHz) δ 7.32 (m, 3H, H10, H2′, H6′); 7.22 (m, 1H, H8); 7.12 (td, J = 7.4 and 1.2 Hz, 1H, H9); 7.00 (td, J = 7.8 and 1.2 Hz, 1H, H7); 6.96 (s, 1H, H2); 6.88 (d, J = 8.5 Hz, 2H, H3′, H5′); 4.61 (t, J = 6.6 Hz, 2H, H5); 4.57 (m, 1H, OCH); 3.83 (s, 3H, OMe); 3.10 (t, J = 6.6 Hz, 2H, H6); 1.37 (d, J = 5.8 Hz, 6H, Me)
36. 3, 400 MHz) δ 7.21 (d, J = 7.4 Hz, 1H, H10); 7.12 (td, J = 7.4 and 1.2 Hz, 1H, H8); 7.01 (td, J = 7.4, 1.2 Hz, H9); 6.96 (d, J = 8.9 Hz, 4H, H2′, H2″, H6′, H6″); 6.94 (td, J = 7.4 and 1.2 Hz, H7); 6.72 (d, J = 8.9 Hz, 4H, H3′, H3″, H5′, H5″); 4.61 (t, J = 6.6 Hz, 2H, H5); 4.50 (q, J = 6.0 Hz, 2H, OCH); 3.59 (s, 3H, OMe); 3.10 (t, J = 6.6 Hz, 2H, H6); 1.31 (d, J = 6.0 Hz, 6H, Me); 1.30 (d, J = 6.0 Hz, 6H, Me)
37. E. Mata Tetrahedron Lett. 38 1997 6335
38. M.G. Banwell, B.L. Flynn, and S.G. Stewart J. Org. Chem. 63 1998 9139
39. 3, 400 MHz) δ 7.28 (m, 3H, H10, H2′, H6′); 7.22 (d, J = 7.4 Hz, 1H, H8); 7.13 (td, J = 7.4 and 1.2, 1H, H9); 7.00 (td, J = 7.4 and 1.2 Hz, 1H, H7); 6.98 (s, 1H, H2); 6.85 (d, J = 8.6 Hz, 2H, H3′, H5′); 4.45 (s, 1H, OH); 4.61 (t, J = 6.6 Hz, 2H, H5); 3.85 (s, 3H, OMe); 3.07 (t, J = 6.6 Hz, 2H, H6)
40. 6, 400 MHz) δ 8.31 (s, 1H, OH); 8. 15 (s, 1H, OH); 7.28 (d, J = 7.4 and 1.2 Hz, 1H, H10); 7.13 (td, J = 7.4 and 1.2 Hz, 1H, H8); 6.97 (td, J = 7.4 and 1.2 Hz, 1H, H9); 6.91 (m, 5H, H2′, H2″, H6′, H6″, H7); 6.70 (dd, J = 8.6 Hz, 2H, H3′, H5′); 6.65 (d, J = 8.6 Hz, 2H, H3″, H5″); 4.57 (t, J = 6.6 Hz, 2H, H5); 3.54 (s, 3H, OMe); 3.11 (t, J = 6.6 Hz, 2H, H6)
41. 2 using KOH as base]
42. K.O. Hessian, and B.L. Flynn Org. Lett. 5 2003 4377
43. T. Hasegawa, K. Yoshida, K. Hachiya, M. Miyazaki, H. Tsuruta, F. Nambu, S. Ohuchida, and M. Kawamura Synlett 1997 511
44. R.A. Fernandes, M.S. Bodas, and P. Kumar Tetrahedron 58 2002 1223
45. S.T. Handy, Y. Zhang, and H. Bregman J. Org. Chem. 69 2004 2362
46. 3, 400 MHz) δ 6.97 (s, 1H, H10); 6.96 (dd, J = 8.0 and 2.0 Hz, 1H, H6′); 6.94 (d, J = 2.0 Hz, 1H, H2′); 6.92 (d, J = 8.0 Hz, 1H, H5′); 6.89 (s, 1H, H7); 6.74 (s, 1H, H2); 5.62 (br s, 1H, OH); 4.60 (t, J = 6.4 Hz, 2H, H5); 4.53 (heptet, J = 6.0 Hz, 1H, OCH); 3.84 (s, 6H, 2 x OMe); 3.42 (s, 3H, OMe); 2.99 (t, J = 6.4 Hz, 2H, H6); 1.37 (d, J = 6.0 Hz, 6H, 2xMe)
47. 3, 400 MHz) δ6.82 (d, J = 8.0 Hz, 1H, H5′); 6.78 (d, J = 8.0 Hz, 1H, H5″); 6.75 (dd, J = 8.0 and 1.6 Hz, 1H, H6′); 6.73 (s, 1H, H10); 6.69 (dd, J = 8.0 and 1.6 Hz, 1H, H6″); 6.68 (s, 1H, H7); 6.57 (d, J = 1.6 Hz, 1H, H2″); 6.56 (d, J = 1.6 Hz, 1H, H2′); 5.58 (s, 1H, OH); 5.54 (s, 1H, OH); 4.61 (t, J = 6.2 Hz, 2H, H5); 4.53 (heptet, J = 6.4 Hz, 1H, OCH); 3.65 (s, 3H, OMe); 3.62 (s, 6H, 2xOMe); 3.33 (s, 3H, OMe); 3.03 (t, J = 6.2 Hz, 1H, H6); 1.36 (d, J = 6.4 Hz, 6H, 2xMe)