Synthesis of enantiopure cis-decahydroquinolines from homotyramines by Birch reduction and aminocyclization

Tetrahedron

Volumn 62, Issue 39, 2006, Pages 9166-9173

  Mena, Marisa ^a   Valls, Nativitat ^a   Borregán, Mar ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Conformational analysis; Decahydroquinolines; Epoxides; Lepadin alkaloids; Nitrogen heterocycles

Indexed keywords

7 OXODECAHYDROQUINOLINE DERIVATIVE; ALKALOID; AMINOALCOHOL; DECAHYDROQUINOLINE DERIVATIVE; DIHYDROANISOLE DERIVATIVE; HOMOTYRAMINE DERIVATIVE; HYDROXYL GROUP; LEPADIN F; LEPADIN G; TYRAMINE; UNCLASSIFIED DRUG;

AMINOCYCLIZATION; ARTICLE; BIRCH REDUCTION; CYCLIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33747008907     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.035     Document Type: Article

References (49)

1. Ueda N., Tokuyama T., and Sakan T. Bull. Chem. Soc. Jpn. 39 (1966) 2012-2014
2. Bonjoch J., Catena J., and Valls N. J. Org. Chem. 61 (1996) 7106-7115
3. Bonjoch J., Catena J., Isábal E., López-Canet M., and Valls N. Tetrahedron: Asymmetry 7 (1996) 1899-1902
4. Bonjoch J., Catena J., Terricabras D., Fernández J.-C., López-Canet M., and Valls N. Tetrahedron: Asymmetry 8 (1997) 3143-3151
5. Valls N., López-Canet M., Vallribera M., and Bonjoch J. Chem.-Eur. J. 7 (2001) 3446-3460
6. Venit J.J., DiPierro M., and Magnus P. J. Org. Chem. 54 (1989) 4298-4301
7. Gensler W.J., Gatsonis C.D., and Ahmed Q.A. J. Org. Chem. 33 (1968) 2968-2971
8. Furstoss R., Esposito G., Teissier P., and Waegell B. Bull. Soc. Chim. Fr. (1974) 2485-2494
9. Adachi J., Nomura K., and Mitsuhashi K. Chem. Pharm. Bull. 24 (1976) 85-91
10. Momose T., Uchida S., Kinoshita M., and Imanishi T. Chem. Pharm. Bull. 25 (1977) 1797-1802
11. Momose T., Uchida S., Kinoshita M., and Imanishi T. Chem. Pharm. Bull. 26 (1978) 620-626
12. Liu D., Wikström H.V., Dijkstra D., deVries J.B., and Venhuis B.J. J. Med. Chem. 49 (2006) 1494-1498
13. For studies of decahydroquinol-7-ones by this strategy in the racemic series, see Ref. 6. For other synthesis of decahydroquinoline derivatives by intramolecular aza-Michael ring closure upon cyclohexenones, see:. Taber D.F., Joshi P.V., and Kanai K. J. Org. Chem. 69 (2004) 2268-2271
14. For Lepadin A, see:. Steffan B. Tetrahedron 47 (1991) 8729-8732
15. For Lepadins B and C, see:. Kubanek J., Williams D.E., de Silva E.D., Allen T., and Anderson R.J. Tetrahedron Lett. 36 (1995) 6189-6192
16. For Lepadins D-F, see:. Wright A.D., Goclik E., König G.M., and Kaminsky R. J. Med. Chem. 45 (2002) 3067-3072
17. For Lepadins F-H, see:. Davis R.A., Carroll A.R., and Quinn R.J. J. Nat. Prod. 65 (2002) 454-457
18. Toyooka N., Okumura M., and Takahatam H. J. Org. Chem. 64 (1999) 2182-2183
19. Toyooka N., Okumura M., Takahatam H., and Nemoto H. Tetrahedron 55 (1999) 10673-10684
20. Osawa T., Aoyagi S., and Kobayashi C. Org. Lett. 2 (2000) 2955-2958
21. Osawa T., Aoyagi S., and Kobayashi C. J. Org. Chem. 66 (2001) 3338-3347
22. Pu X., and Ma D. Angew. Chem., Int. Ed. 43 (2004) 4222-4225
23. Kalai C., Tate E., and Zard S.Z. Chem. Commun. (2002) 1430-1431
24. For a previous work in this field, see:. Mena M., and Bonjoch J. Tetrahedron 61 (2005) 8264-8270
25. Sato S., Aoyagi S., and Kibayashi C. Org. Lett. 5 (2003) 3839-3842
26. Cassidy M.P., and Padwa A. Org. Lett. 6 (2004) 4029-4031
27. Tsai M.-R., Chen B.-F., Cheng C.-C., and Chang N.-C. J. Org. Chem. 70 (2005) 1780-1785
28. Lemire A., and Charette A.B. Org. Lett. 7 (2005) 4029-4031
29. For a review in the chemistry of N,N-dibenzylamino aldehydes, see:. Reetz M.T. Chem. Rev. 99 (1999) 1121-1162
30. For the formation of syn-amino alcohols in the reduction of N,N-dibenzyl α-alkyl-α-amino ketones, see:. Hart S.A., Sabat M., and Etzkorn F.A. J. Org. Chem. 63 (1998) 7580-7581
31. For a review in the chemistry of N-protected-α-amino aldehydes, see:. Gryko D., Chalko J., and Jurczak J. Chirality 15 (2003) 514-541
32. Ibuka T., Habashita H., Otaka A., Fujii N., Oguchi Y., Uyehara T., and Yamamoto Y. J. Org. Chem. 56 (1991) 4370-4382
33. Angle S.R., Breitenbucher J.G., and Arnaiz D.O. J. Org. Chem. 57 (1992) 5947-5955
34. Kumar K.K., and Datta A. Tetrahedron 55 (1999) 13899-13906
35. Randl S., and Blechert S. Tetrahedron Lett. 45 (2004) 1167-1169
36. 20 was here reported by reaction of tribenzyl alanine with N,O-dimethylhydroxylamine using isopropylmagnesium chloride according to a protocol introduced by. Williams J.M., Jobson R.B., Yasuda N., Marchesini G., Dolling U.-H., and Grabowski E.J.J. Tetrahedron Lett. 36 (1995) 5461-5464
37. Beaulieu P.L., and Wernic D. J. Org. Chem. 61 (1996) 3635-3645
38. Barluenga J., Baragaña B., and Concellón J.-M. J. Org. Chem. 60 (1995) 6696-6699
39. Eis M.J., Wrobel J.E., and Ganem B. J. Am. Chem. Soc. 106 (1984) 3693-3694
40. 2O, see Ref. 13. For the reductive alkylation of epoxide 3 with organolithium reagents, see:. Concellón J.M., Suárez J.R., and Del Solar V. Org. Lett. 8 (2006) 349-351
41. {A figure is presented}
42. Reetz M.T., Drewes M.W., Lennick K., Schmitz A., and Holdgrün X. Tetrahedron: Asymmetry 1 (1990) 375-378
43. For NMR studies of decahydroquinolines, see:
44. Eliel E.L., and Vierhapper F.W. J. Org. Chem. 41 (1976) 199-208
45. Vierhapper F.W., and Eliel E.L. J. Org. Chem. 42 (1977) 51-62
46. Spande T.F., Jain P., Garraffo H.M., Pannell L.K., Yeh H.J.C., Daly J.W., Fukumoto S., Imamura K., Torres J.A., Snelling R.R., and Jones T.H. J. Nat. Prod. 62 (1999) 5-21
47. Phuan P.-W., and Kozlowski M.C. J. Org. Chem. 67 (2002) 6339-6346
48. Reetz M.T., Drewes M.W., and Schmitz A. Angew. Chem., Int. Ed. Engl. 26 (1987) 1141-1143
49. Reetz M.T., Drewes M.W., and Schwickardi R. Org. Synth. 76 (1999) 110-122