Intramolecular chemoselective acylation of a suitably substituted isoindole: Synthesis of (±)-chilenine and (±)-deoxychilenine

Synthesis

Volumn , Issue 17, 2011, Pages 2838-2842

  Wakchaure, Prasad B ^a   Argade, Narshinha P ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

chemoselective acylation; chilenine; deoxychilenine; homophthalic anhydride; isoindole; total synthesis

Indexed keywords

CHEMOSELECTIVE ACYLATION; CHILENINE; DEOXYCHILENINE; HOMOPHTHALIC ANHYDRIDE; ISOINDOLE; TOTAL SYNTHESIS;

ACYLATION;

12 HYDROXY 9,10 DIMETHOXY 5H [1,3] DIOXOLO [4'',5'':4',5'] BENZO [1',2':4,5] AZEPINO [2,1 ALPHA] ISOINDOLE 8,13 (6H,12H) DIONE; 2 [2 (1,3 BENZODIOXOL 5 YL)ETHYL] 7,8 DIMETHOXYISOQINOLINE 1,3 (2H) TRIONE; 2 [2 (1,3 BENZODIOXOL 5 YL)ETHYL] 7,8 DIMETHOXYISOQINOLINE 1,3 (2H,4H) DIONE; 2 [2 (6 BROMO 1,3 BENZODIOXOL 5 YL)ETHYL] 7,8 DIMETHOXYISOQINOLINE 1,3 (2H) TRIONE; 2 [2 (6 BROMO 1,3 BENZODIOXOL 5 YL)ETHYL] 7,8 DIMETHOXYISOQINOLINE 1,3 (2H,4H) DIONE; 9,10 DIMETHOXY 5H [1,3] DIOXOLO [4'',5'':4',5'] BENZO [1',2':4,5] AZEPINO [2,1 ALPHA] ISOINDOLE 8,13 (6H,12H) DIONE; 9,10,12 TRIMETHOXY 5H [1,3] DIOXOLO [4'',5'':4',5'] BENZO [1',2':4,5] AZEPINO [2,1 ALPHA] ISOINDOLE 8,13 (6H,12H) DIONE; CHILENINE; DEOXYCHILENINE; ISOINDOLE DERIVATIVE; LENNOXAMINE; METHYL 2 [2 (1,3 BENZODIOXOL 5 YL)ETHYL] 1 HYDROXY 4,5 DIMETHOXY 3 OXO 2,3 DIHYDRO 1H ISOINDOLE 1 CARBOXYLATE; METHYL 2 [2 (6 BROMO 1,3 BENZODIOXOL 5 YL)ETHYL] 1 HYDROXY 4,5 DIMETHOXY 3 OXO 2,3 DIHYDRO 1H ISOINDOLE 1 CARBOXYLATE; METHYL 2 [2 (6 BROMO 1,3 BENZODIOXOL 5 YL)ETHYL] 1,4,5 TRIMETHOXY 3 OXO 2,3 DIHYDRO 1H ISOINDOLE 1 CARBOXYLATE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION;

EID: 80052066954     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260140     Document Type: Article

References (47)

1. Valencia E, Freyer A J., Shamma M, Fajardo V, Tetrahedron Lett. 1984 25 599
2. Valencia E, Weiss I, Firdous S, Freyer A J., Shamma M, Tetrahedron 1984 40 3957
3. Fajardo V, Elango V, Cassels B K., Shamma M, Tetrahedron Lett. 1982 23 39
4. Boltukhina E V., Zubkov F I., Varlamov A V., Chem. Heterocycl. Compd. (Engl. Transl.) 2006 42 831; and references cited therein
5. Moniot J L., Hindenlang D M., Shamma M, J. Org. Chem. 1979 44 4343
6. Moniot J L., Hindenlang D M., Shamma M, J. Org. Chem. 1979 44 4347
7. Elango V, Shamma M, J. Org. Chem. 1983 48 4879
8. Kim G, Jung P, Tuan L A., Tetrahedron Lett. 2008 49 2391
9. Fuwa H, Sasaki M, Org. Biomol. Chem. 2007 5 1849
10. Honda T, Sakamaki Y, Tetrahedron Lett. 2005 46 6823
11. Kim G, Kim J H., Kim W.-J, Kim Y A., Tetrahedron Lett. 2003 44 8207
12. Yoda H, Inoue K.-I, Ujihara Y, Mase N, Takabe K, Tetrahedron Lett. 2003 44 9057
13. Koseki Y, Katsura S, Kusano S, Sakata H, Sato H, Monzene Y, Nagasaka T, Heterocycles 2003 59 527
14. Yoda H, Nakahama A, Koketsu T, Takabe K, Tetrahedron Lett. 2002 43 4667
15. Padwa A, Beall L S., Eidell C K., Worsencroft K J., J. Org. Chem. 2001 66 2414
16. Koseki Y, Kusano S, Sakata H, Nagasaka T, Tetrahedron Lett. 1999 40 2169
17. Ishibashi H, Kawanami H, Ikeda M, J. Chem. Soc., Perkin Trans. 1 1997 817
18. Ishibashi H, Kawanami H, Iriyama H, Ikeda M, Tetrahedron Lett. 1995 36 6733
19. Fang F G., Danishefsky S J., Tetrahedron Lett. 1989 30 2747
20. Mazzocchi P H., King C R., Ammon H L., Tetrahedron Lett. 1987 28 2473
21. Dorn C R., Koszyk F J., Lenz G R., J. Org. Chem. 1984 49 2642
22. Shamma M, Moniot J L., Hindenlang D M., Tetrahedron Lett. 1977 18 4273
23. Li L, Wang M, Zhang X, Jiang Y, Ma D, Org. Lett. 2009 11 1309
24. Onozaki Y, Kurono N, Senboku H, Tokuda M, Orito K, J. Org. Chem. 2009 74 5486
25. Couty S, Liegault B, Meyer C, Cossy J, Tetrahedron 2006 62 3882
26. Suzuki T, Takabe K, Yoda H, Synlett 2006 3407
27. Couty S, Meyer C, Cossy J, Tetrahedron Lett. 2006 47 767
28. Taniguchi T, Iwasaki K, Uchiyama M, Tamura O, Ishibashi H, Org. Lett. 2005 7 4389
29. Comins D L., Schilling S, Zhang Y, Org. Lett. 2005 7 95
30. Sahakitpichan P, Ruchirawat S, Tetrahedron 2004 60 4169
31. Fuchs J R., Funk R L., Org. Lett. 2001 3 3923
32. Ruchirawat S, Sahakitpichan P, Tetrahedron Lett. 2000 41 8007
33. Rodriguez G, Cid M M., Saa C, Castedo L, Dominguez D, J. Org. Chem. 1996 61 2780
34. Moody C J., Warrellow G J., J. Chem. Soc., Perkin Trans. 1 1990 2929
35. Moody C J., Warrellow G J., Tetrahedron Lett. 1987 28 6089; and references cited therein
36. Batwal R U., Patel R M., Argade N P., Tetrahedron: Asymmetry 2011 22 173
37. Kshirsagar U A., Puranik V G., Argade N P., J. Org. Chem. 2010 75 2702
38. Kshirsagar U A., Argade N P., Tetrahedron 2009 65 5244
39. Wakchaure P B., Easwar S, Argade N P., Synthesis 2009 1667
40. Haval K P., Argade N P., J. Org. Chem. 2008 73 6936; and references cited therein
41. Wakchaure P B., Easwar S, Puranik V G., Argade N P., Tetrahedron 2008 64 1786
42. Wakchaure P B., Puranik V G., Argade N P., Tetrahedron: Asymmetry 2009 20 220; and references cited therein
43. Parham W E., Jones L D., Sayed Y, J. Org. Chem. 1975 40 2394
44. Faltz H, Bender C, Liebscher J, Synthesis 2006 2907
45. Lage S, Villaluenga I, Sotomayor N, Lete E, Synlett 2008 3188
46. Gonzalez-Lopez M, Shaw J T., Chem. Rev. 2009 109 164; and references cited therein
47. DeSilva S O., Ahmad I, Snieckus V, Tetrahedron Lett. 1978 19 5107