Regioselective monoalkylation of dimethyl alkylidenesuccinates: Simple approach to dialkyl-substituted maleic anhydrides including chaetomellic acid A

Synthesis

Volumn , Issue 11, 2011, Pages 1804-1808

  Kshirsagar, Umesh A ^a   Argade, Narshinha P ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

alkylations; esters; furans; heterocycles; maleic anhydrides

Indexed keywords

BASE-CATALYZED HYDROLYSIS; FURANS; HETEROCYCLES; MONOALKYLATION; REGIO-SELECTIVE; SIMPLE APPROACH;

SODIUM;

MALEIC ANHYDRIDE;

ALKYL GROUP; BASE; CHAETOMELLIC ACID A; CHEMICAL COMPOUND; DIMETHYL ALKYLIDENESUCCINATE; MALEIC ANHYDRIDE; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; HYDROLYSIS; SYNTHESIS;

EID: 79956372411     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260013     Document Type: Article

References (62)

1. Chen X, Zheng Y, Shen Y, Chem. Rev. 2007 107 1777
2. Li D, Liu G, Hu Q, Wang C, Xi Z, Org. Lett. 2007 9 5433
3. Oishi T, Gao H, Nakamura T, Isobe Y, Onimura K, Polym. J. (Tokyo, Jpn.) 2007 39 1047
4. Scholte A A., Eubanks L M., Poulter C D., Vederas J C., Bioorg. Med. Chem. 2004 12 763; and references cited therein
5. Wong K C., Tan G L., Flavour Fragrance J. 1994 9 25
6. Boesel R, Schilcher H, Planta Med. 1989 55 399
7. Poll L, Lewis M J., Lebensm.-Wiss. Technol. 1986 19 258
8. Singh S B., Zink D L., Liesch J M., Goetz M A., Jenkins R G., Nallin-Omstead M, Silverman K C., Bills G F., Mosley R T., Gibbs J B., Albers-Schonberg G, Lingham R B., Tetrahedron 1993 49 5917
9. Assante G, Camarda L, Merlini L, Nasini G, Gazz. Chim. Ital. 1979 109 151
10. Cheng X.-C, Kihara T, Kusakabe H, Magae J, Kobayashi Y, Fang R.-P, Ni Z.-F, Shen Y.-C, Ko K, Yamaguchi I, Isono K, J. Antibiot. 1987 40 907
11. Cheng X.-C, Ubukata M, Isono K, J. Antibiot. 1990 43 890
12. Cheng X.-C, Ubukata M, Kiyoshi I, J. Antibiot. 1990 43 809
13. Kinoshira K, Nakajima S, Chem. Pharm. Bull. 1958 6 31
14. Miyagawa H, Hamada N, Sato M, Ueno T, Phytochemistry 1994 36 1319
15. Adeboya M O., Edwards R L., Laessoe T, Maitland D J., Whalley A J. S., Liebigs Ann. Chem. 1996 1437
16. Weidenmüller H.-L, Cavagna F, Fehlhaber H.-W, Präve P, Tetrahedron Lett. 1972 3519
17. Itoh S, Esaki N, Masaki K, Blank W, Soda K, J. Ferment. Bioeng. 1994 77 513
18. Dardennes E, Labano S, Simpkins N S., Wilson C, Tetrahedron Lett. 2007 48 6380
19. Alizadeh A, Movahedi F, Esmaili A A., Tetrahedron Lett. 2006 47 4469
20. Kishorebabu N, Periasamy M, Tetrahedron Lett. 2006 47 2107
21. Bellesia F, Danieli C, De Buyck L, Galeazzi R, Ghelfi F, Mucci A, Orena M, Pagnoni U M., Parsons A F., Roncaglia F, Tetrahedron 2006 62 746
22. De Buyck L, Danieli C, Ghelfi F, Pagnoni U M., Parsons A F., Pattarozzi M, Roncaglia F, Tetrahedron 2005 61 2871
23. Brown G D., Wong H.-F, Tetrahedron 2004 60 5439
24. Kurono M, Isobe M, Tetrahedron 2004 60 1773
25. Spiegel D A., Njardarson J T., McDonald I M., Wood J L., Chem. Rev. 2003 103 2691
26. Nicolaou K C., Zhong Y L., Baran P S., Jung J, Choi H S., Yoon W H., J. Am. Chem. Soc. 2002 124 2202
27. Adlington R M., Baldwin J E., Cox R J., Pritchard G J., Synlett 2002 820
28. Bellina F, Rossi R, Synthesis 2002 2729
29. Tan Q, Danishefsky S J., Angew. Chem. Int. Ed. 2001 40 647
30. Chen C, Layton M E., Sheehan S M., Shair M D., J. Am. Chem. Soc. 2000 122 7424
31. White J D., Kim J, Drapela N E., J. Am. Chem. Soc. 2000 122 8665
32. Yoshimitsu T, Yanagisawa S, Nagaoka H, Org. Lett. 2000 2 3751; and references cited therein
33. Haval K P., Argade N P., J. Org. Chem. 2008 73 6936
34. Easwar S, Argade N P., Synthesis 2006 831
35. Kar A, Argade N P., Tetrahedron 2003 59 2991
36. Kar A, Argade N P., J. Org. Chem. 2002 67 7131
37. Kar A, Argade N P., Tetrahedron Lett. 2002 43 6563
38. Mangaleswaran S, Argade N P., J. Org. Chem. 2001 66 5259
39. Mangaleswaran S, Argade N P., J. Chem. Soc., Perkin Trans. 1 2001 1764
40. Deshpande A M., Natu A A., Argade N P., Synthesis 2001 702
41. Deshpande A M., Natu A A., Argade N P., J. Org. Chem. 1998 63 9557
42. Desai S B., Argade N P., J. Org. Chem. 1997 62 4862; and references cited therein
43. Batwal R U., Patel R M., Argade N P., Tetrahedron: Asymmetry 2011 22 173
44. Patel R M., Argade N P., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2010 49 1071
45. Kshirsagar U A., Puranik V G., Argade N P., J. Org. Chem. 2010 75 2702
46. Patel R M., Argade N P., Synthesis 2009 372
47. Kshirsagar U A., Argade N P., Tetrahedron 2009 65 5244
48. Wakchaure P B., Easwar S, Puranik V G., Argade N P., Tetrahedron 2008 64 1786
49. Patel R M., Argade N P., J. Org. Chem. 2007 72 4900
50. Hedaya E, Theodoropulos S, Tetrahedron 1968 24 2241
51. Huanfeng J, Wei W, Weibing L, Chunli Q, Chin. J. Chem. 2010 28 263
52. Bilenko V, Jiao H, Spannenberg A, Fischer C, Reinke H, Kösters J, Komarov I, Börner A, Eur. J. Org. Chem. 2007 758
53. Moroy G, Denhez C, Mourabit H E., Toribio A, Dassonville A, Decarme M, Renault J.-H, Mirand C, Bellon G, Sapi J, Alix A J. P., Hornebeck W, Bourguet E, Bioorg. Med. Chem. 2007 15; 4753
54. McCombie S W., Luchaco C A., Tetrahedron Lett. 1997 38 5775; and references cited therein
55. Ballini R, Bosica G, Fiorini D, Gil M V., Palmieri A, Synthesis 2004 605
56. Ballini R, Bosica G, Palmieri A, Petrini M, Pierantozzi C, Tetrahedron 2003 59 7283
57. Ballini R, Bosica G, Tetrahedron 1995 51 4231
58. Ballini R, Rinaldi A, Tetrahedron Lett. 1994 35 9247
59. Tsui W Y., Williams G A., Brown G D., Phytochemistry 1996 43 1083
60. Lee S C., Brown G D., J. Nat. Prod. 1998 61 29
61. Brown G D., Wong H F., Tetrahedron 2004 60 5439
62. Kar A, Gogoi S, Argade N P., Tetrahedron 2005 61 5297