Mechanistic investigation of the domino oxy-cope/ene/claisen reaction and its application to the synthesis of desdimethyl ambliol B

Synthesis (Germany)

Volumn 44, Issue 12, 2012, Pages 1833-1840

  Barriault, Louis ^a   Denissova, Irina ^a   Goulet, Nathalie ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

diastereoselectivity; domino; macrocycle; oxy Cope ene Claisen; sigmatropic

Indexed keywords

DIASTEREO-SELECTIVITY; DOMINO; MACROCYCLES; OXY-COPE/ENE/CLAISEN; SIGMATROPIC;

ORGANIC SOLVENTS;

STEREOSELECTIVITY;

1 (FURAN 3 YL) 2 (4A HYDROXY 1,2 DIMETHYLDECAHYDRONAPHTHALEN 1 YL)ETHYL ACETIC ACID; 1 [1 (ALLYLOXY)BUT 2 EN 2 YL] 2 CHLOROCYCLOHEXANOL; 1 [2 (FURAN 3 YL) 2 HYDROXYETHYL] 1,2 DIMETHYLDECAHYDRONAPHTHALEN 4A OL; 1 [4 [4A HYDROXY 1,2 DIMETHYLDECAHYDRONAPHTHALEN 1 YL]BUT 2 ENYL] 1,2 DIMETHYDECAHYDRONAPHTHALEN 4A OL; 1 ALLYL 4 (ETHYLTHIO) 1,2 DIMETHYLDECAHYDRONAPHTHALEN 4A OL; 1 ALLYL 4 (ETHYLTHIO) 2 METHYLOCTAHYDRO 1H 4A,1 (EPOXYMETHANO)NAPHTHALEN 10 OL; 2 (4A HYDROXY 1,2 DIMETHYLDECAHYDRONAPHTHALEN 1 YL)ACETALDEHYDE; 2 [1 (ALLYLOXY)BUT 2 EN 2 YL] 1 [1 (ETHYLTHIO)VINYL]CYCLOHEXANOL; 2 [1 (ALLYLOXY)BUT 2 EN 2 YL] 2 CYCLOHEXANONE; 2 METHYL 1 METHYLENE 4 PHENYLDECAHYDRONAPHTHALEN 4A OL; 2 METHYL 1 METHYLENEDECAHYDRONAPHTHALEN 4A OL; 2,4 DIMETHYL 1 METHYLENEDECAHYDRONAPHTHALEN 4A OL; 4 (ETHYLTHIO) 1 [4 [4 (ETHYLTHIO) 4A HYDROXY 1,2 DIMETHYLDECAHYDRONAPHTHALEN 1 YL]BUT 2 ENYL] 1,2 DIMETHYDECAHYDRONAPHTHALEN 4A OL; 4 (ETHYLTHIO) 2 METHYL 1 METHYLENEDECAHYDRONAPHTHALEN 4A OL; DECALIN DERIVATIVE; DESDIMETHYL AMBLIOL B; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; COPE REARRANGEMENT; DOMINO REACTION; ENE REACTION; FEASIBILITY STUDY; OXY COPE REARRANGEMENT; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 84861850295     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1291144     Document Type: Article

References (48)

1. Tietze LF, Brasche G, Gericke K. Domino Reactions in Organic Synthesis. Wiley-VCH Weinheim: 2006
2. Poulin J, Grisé-Bard CM, Barriault L. Chem. Soc. Rev.: 2009; 38 3092
3. Nicolaou KC, Chen JS. Chem. Soc. Rev.: 2009; 38 2993
4. Padwa A. Chem. Soc. Rev.: 2009; 38 3072
5. Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed.: 2006; 45 7134
6. Arns S, Barriault L. Chem. Commun.: 2007; 2211
7. Fuji K. Chem. Rev.: 1993; 93 2037
8. Corey EJ, Guzman-Perez A. Angew. Chem. Int. Ed.: 1998; 37 388
9. Christoffers J, Mann A. Angew. Chem. Int. Ed.: 2001; 40 4591
10. Denissova I, Barriault L. Tetrahedron: 2003; 59 10105
11. Ramon DJ, Yus M. Curr. Org. Chem.: 2004; 8 149
12. Christoffers J, Baro A. Adv. Synth. Catal.: 2005; 447 1473
13. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis. Christoffers J, Baro A. Wiley-VCH Weinheim: 2005
14. Trost BM, Jiang C. Synthesis: 2006; 369
15. Cozzi PG, Hilgraf R, Zimmermann N. Eur. J. Org. Chem.: 2007; 5969
16. Bella M, Gasperi T. Synthesis: 2009; 1583
17. Kumagai N. Chem. Pharm. Bull.: 2011; 59 1
18. Corey EJ, Roberts BE. J. Am. Chem. Soc.: 1997; 119 12425
19. Boukouvalas J, Cheng Y, Robichaud J. J. Org. Chem.: 1998; 63 288
20. Magnuson SR, Sepp-Lorenzino L, Rosen N, Danishefsky SJ. J. Am. Chem. Soc.: 1998; 120 1615
21. Demeke D, Forsyth CJ. Org. Lett.: 2000; 2 3177
22. Piers E, Caillé S, Chen G. Org. Lett.: 2000; 2 2483
23. Paczkowski R, Maichle-Mössmer C, Maier ME. Org. Lett.: 2000; 2 3967
24. Takahashi M, Dodo K, Hashimoto Y, Shirai R. Tetrahedron Lett.: 2000; 41 2111
25. Miyaoka H, Kajiwara Y, Yamada Y. Tetrahedron Lett.: 2000; 41 911
26. Miyaoka H, Kajiwara Y, Hara Y, Yamada Y. J. Org. Chem.: 2001; 66 1429
27. Jung ME, Nishimura N. Org. Lett.: 2001; 3 2113
28. Demeke D, Forsyth CJ. Tetrahedron: 2002; 58 6531
29. Ohba M, Kawase N, Fujii T. J. Am. Chem. Soc.: 1996; 118 8250
30. Ohba M, Iizuka K, Ishibashi H, Fujii T. Tetrahedron: 1997; 53 16977
31. Barriault L, Denissova I. Org. Lett.: 2002; 4 1371
32. Farand JA, Denissova I, Barriault L. Heterocycles: 2004; 62 735
33. Curtin DY. Rec. Chem. Prog.: 1954; 15 111
34. Winstein S, Holness NJ. J. Am. Chem. Soc.: 1955; 77 5562
35. Eliel EL. Stereochemistry of Carbon Compounds. McGraw-Hill New York: 1962
36. Hammett LP. Physical Organic Chemistry. McGraw-Hill New York: 1970; Chap. 5
37. Seeman JI. Chem. Rev.: 1983; 83 83
38. Still WC, Galynker I. Tetrahedron: 1981; 37 3981
39. Still WC. J. Am. Chem. Soc.: 1977; 99 4186
40. Still WC. J. Am. Chem. Soc.: 1979; 101 2493
41. Still WC. In Current Trends in Organic Synthesis. Nozaki H. IUPAC-Pergamon Press Oxford: 1983; 233
42. Still WC, Murata S, Revial G, Yoshihara K. J. Am. Chem. Soc.: 1983; 105 625
43. Still WC, Novack VJ. J. Am. Chem. Soc.: 1984; 106 1148
44. Still WC, Romero AG. J. Am. Chem. Soc.: 1986; 108 2105
45. Arns S, Denissova I, Lebrun M.-E, Grisé CM, Barriault L. J. Org. Chem.: 2007; 72 9314
46. Barriault L, Sauer EL. O. J. Am. Soc. Chem.: 2004; 126 8569
47. Barriault L, Sauer EL. O, Hooper J, Woo T. J. Am. Chem. Soc.: 2007; 129 2112
48. Hooper J, Sauer EL. O, Arns S, Woo TK, Barriault L. Chem.-Eur. J.: 2010; 16 14124