A synthetic view of an analogue of the spiro-β-lactone-γ-lactam ring in oxazolomycins and lajollamycin

Synthesis

Volumn , Issue 19, 2010, Pages 3301-3308

  Mondal, Dhananjoy ^a   Bera, Smritilekha ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Crimmins aldol reaction; Crossed Cannizzaro reaction; Garners aldehyde; Lactones; Mitsunobu reaction; Pyrrolidine

Indexed keywords

CANNIZZARO REACTION; CRIMMINS ALDOL REACTION; GARNERS ALDEHYDE; LACTONES; MITSUNOBU REACTIONS; PYRROLIDINES;

CHLORINE COMPOUNDS; CONDENSATION REACTIONS; TITANIUM;

ALDEHYDES;

3 (BENZYLOXY) 1 (TERT BUTYLCARBONYL) 2 (HYDROXYMETHYL) 4 METHYLPYRROLIDINE 2 CARBOXYLIC ACID; 3 (BENZYLOXY) 2 (HYDROXYMETHYL) 4 METHYLPYRROLIDINE 2 CARBOXYLIC ACID; 7 (BENZYLOXY) 7A (HYDROXYMETHYL) 6 METHYLTETRAHYDROPYRROLO[1,2 C]OXAZOL 3(1H) ONE; ALDEHYDE; ANTIBIOTIC AGENT; CARBAMIC ACID DERIVATIVE; FORMALDEHYDE; GAMMA LACTAM DERIVATIVE; GARNER ALDEHYDE; HYDROXYL GROUP; LACTONE; LAJOLLAMYCIN; METHYL 7 (BENZYLOXY) 6 METHYL 3 OXOHEXAHYDROPYRROLO[1,2 C]OXAZOLE 7A CARBOXYLATE; OXAZOLOMYCIN; OXAZOLOMYCIN A; OXAZOLOMYCIN B; OXAZOLOMYCIN C; REAGENT; SPIRO BETA LACTONE; TERT BUTYL 3 (BENZYLOXY) 2 (HYDROXYMETHYL) 4 METHYLPYRROLIDINE 1 CARBOXYLATE; TERT BUTYL 4 (1,3 DIHYDROXY 2 METHYLPROPYL) 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [1 (BENZYLOXY) 2 METHYL 3 (4 TOLUENESULFONYLOXY)PROPYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [1 (BENZYLOXY) 3 (TERT BUTYLDIMETHYLSILOXY) 2 METHYLPROPYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [1 (BENZYLOXY) 3 HYDROXY 2 METHYLPROPYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [3 (4 BENZYL 2 OXOOXAZOLIDIN 3 YL) 1 HYDROXY 2 METHYL 3 OXOPROPYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 4 [3 (TERT BUTYLDIMETHYLSILOXY) 1 HYDROXY 2 METHYLPROPYL] 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; TERT BUTYL 8 (BENZYLOXY) 7 METHYL 1 OXO 2 OXA 5 AZASPIRO[3.4]OCTANE 5 CARBOXYLATE; TITANIUM CHLORIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CANNIZZARO REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHELATION; CRIMMINS ALDOL REACTION; CYCLIZATION; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MITSUNOBU REACTION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SHARPLESS ASYMMETRIC DIHYDROXYLATION; SWERN OXIDATION; TAYLOR OXIDATION; WITTIG REACTION;

EID: 77957112116     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1257872     Document Type: Article

References (50)

1. Moloney M G., Trippier P C., Yaqoob M, Wang Z, Curr. Drug Discovery Technol. 2004 1 181
2. Mori T, Takahashi K, Kashiwabara M, Uemura D, Katayama C, Iwadare S, Shizuri Y, Mitomo R, Nakano F, Matsuzaki A, Tetrahedron Lett. 1985 26 1073
3. Takahashi K, Kawabata M, Uemura D, Iwadare S, Mitomo R, Nakano F, Matsuzaki A, Tetrahedron Lett. 1985 26 1077
4. Kanzaki H, Wada K, Nitoda T, Kawazu K, Biosci., Biotechnol., Biochem. 1998 62 438
5. Kawazu K, Kanzaki H, Kawabata G, Kawai S, Kobayashi A, Agric. Biol. Chem. 1989 53 1127
6. Tonew E, Tonew M, Grfe U, Zpel P, Acta Virol. 1992 36 166
7. Bagwell C L., Moloney M G., Thompson A L., Bioorg. Med. Chem. Lett. 2008 18 4081
8. Ryu G, Hwang S, Kim S K., J. Antibiot. 1997 50 1064
9. Ogura M, Tanaka T, Furihata K, Shimazu A, Otake N, J. Antibiot. 1986 39 1443
10. Otani T, Yoshida K I., Kubota H, Kawai S, Ito S, Hori H, Ishiyama T, Oki T, J. Antibiot. 2000 53 1397
11. Manam R R., Teisan S, White D J., Nicholson B, Grodberg J, Neuteboom S T. C., Lam K S., Mosca D A., Lloyd G K., Potts B C. M., J. Nat. Prod. 2005 68 240
12. Kende A S., Kawamura K, DeVita R J., J. Am. Chem. Soc. 1990 112 4070
13. Onyango E O., Tsurumoto J, Imai N, Takahashi K, Ishihara J, Hatakeyama S, Angew. Chem. Int. Ed. 2007 46 6703
14. Kende A S., Kawamura K, Orwat M J., Tetrahedron Lett. 1989 30 5821
15. Kende A S., Kawamura K, DeVita R J., J. Am. Chem. Soc. 1990 112 4072
16. Hnaff N, Whiting A, Org. Lett. 1999 1 1137
17. Bulger P G., Moloney M G., Trippier P C., Synlett 2002 1871
18. Bulger P G., Moloney M G., Trippier P C., Org. Biomol. Chem. 2003 1 3726
19. Mohapatra D K., Mondal D, Gonnade R G., Chorghade M S., Gurjar M K., Tetrahedron Lett. 2006 47 6031
20. Papillon J P. N., Taylor R J. K., Org. Lett. 2000 2 1987
21. Donohoe T J., Chiu J Y. K., Thomas R E., Org. Lett. 2007 9 421
22. Bennett N J., Prodger J C., Pattenden G, Tetrahedron 2007 63 6216
23. Yamada T, Sakaguchi K, Shinada T, Ohfune Y, Soloshonok V A., Tetrahedron: Asymmetry 2008 19 2789
24. Evans D A., Reiger D L., Bilodeau M T., Urpi F, J. Am. Chem. Soc. 1991 113 1047
25. Crimmins M T., King B W., Tabet E A., Chaudhary K, J. Org. Chem. 2001 66 894
26. Ho G J., Mathre D J., J. Org. Chem. 1995 60 2271
27. Ager D J., Prakash I, Schaad D R., Chem. Rev. 1996 96 835
28. Garner P, Tetrahedron Lett. 1984 25 5855
29. Jurczak J, Golebiowski A, Chem. Rev. 1989 89 149
30. Liang K, Andersch J, Bols M, J. Chem. Soc., Perkin Trans. 1 2001 2136; and references cited therein
31. Mitsunobu O, Synthesis 1981 1
32. Lall M S., Ramtohul Y K., James M N. G., Vederas J C., J. Org. Chem. 2002 67 1536
33. Mohapatra D K., Mondal D, Chorghade M S., Gurjar M K., Tetrahedron Lett. 2006 47 9215
34. Evans D A., Kaldor S W., Jones T K., Clardy J, Stout T J., J. Am. Chem. Soc. 1990 112 7001
35. Iseki K, Oishi S, Kobayashi Y, Tetrahedron 1996 52 71
36. Clive D L. J., Yu M, Chem. Commun. 2002 2380
37. Zhang W, Carter R G., Yokochi A F. T., J. Org. Chem. 2004 69 2569
38. Youssefyeh R D., Verheyden J P. H., Moffatt J G., J. Org. Chem. 1979 44 1301
39. Shimida K, Kaburagi Y, Fukuyama T, J. Am. Chem. Soc. 2003 125 4048
40. Williams D R., Klingler F D., Allen E D., Lichtenthaler F W., Tetrahedron Lett. 1998 29 5087
41. Bakke J M., Frhaug A E., Acta Chem. Scand. 1995 49 615
42. Bakke J M., Frhaug A E., J. Phys. Org. Chem. 1996 9 310
43. Han J.-S, Lowary T L., J. Org. Chem. 2003 68 4116
44. Trifilieff E, Bang L, Narula A S., Ourisson G, J. Chem. Res., Miniprint 1978 601
45. Muller P, In Chemistry of Functional Groups Suppl. E, Part 1 Patai S Wiley New York 1980 469
46. Wan P, Tetrahedron Lett. 1985 26 2387
47. Bodwell G J., Li J, Angew. Chem. Int. Ed. 2002 41 3261
48. Henbest H B., Nicholls B, J. Chem. Soc. 1959 227
49. Carlsen H J., Katsuki T, Martin V S., Sharpless K B., J. Org. Chem. 1981 46 3936
50. Naota T, Takaya H, Murahashi S.-I, Chem. Rev. 1998 98 2599