New route to N-alkylated trans-pyrrolidine diols from 2,2,3,3- tetramethoxybutane-protected dimethyl tartrate

Synthetic Communications

Volumn 38, Issue 9, 2008, Pages 1365-1374

  Martins, J Graça ^a   Barrulas, P Cambeiro ^a   Marques, Carolina S ^a   Burke, Anthony J ^a  

^a UNIVERSITY OF ÉVORA   (Portugal)

Author keywords

Alkylation; Azidation; Cyclization; Dihydroxylated indolizidines

Indexed keywords

1 ALLYL 3,4 PYRROLIDINEDIOL; 1 BENZYL 3,4 PYRROLIDINEDIOL; 1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2,2,3,3 TETRAMETHOXYBUTANE; 5,6 DIMETHOXY 5,6 DIMETHYL[1,4]DIOXANE 2,3 DICARBOXYLIC ACID DIMETHYL ESTER; AZIDE; DIMETHYL TARTRATE; PYRROLIDINE DERIVATIVE; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; BIOASSAY; CATALYSIS; CYCLIZATION; CYTOTOXICITY TEST; HYDROGENATION;

EID: 42149109718     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801916520     Document Type: Article

References (33)

1. For a good review, see. Cardona, F.; Goti, A.; Brandi, A. (+)-Lentiginosine, a potent and selective inhibitor of amyloglucosidase: Synthetic efforts and disputes on its absolute configuration. Eur. J. Org. Chem. 2007, 1551-1565.
2. Ballini, R.; Marcantoni, E.; Petrini, M. A. A nitrone based approach to the enantioselective total synthesis of (-)-anisomycin. J. Org. Chem. 1992, 57, 1316.
3. Inverarity, I. A.; Hulme, A. N. Marked small molecule libraries: A truncated approach to molecular probe design. Org. Biomol. Chem. 2007, 5, 636-643.
4. Hutin, P.; Haddad, M.; Larchevêque, M. Stereoselective synthesis of (-)-deacetylanisomycin. Tetrahedron: Asymmetry 2000, 11, 2547-2553.
5. Murruzzu, C.; Riera, A. Enantioselective synthesis of hydroxylated pyrrolidines via sharpless epoxidation and olefin metathesis. Tetrahedron: Asymmetry 2007, 18, 149;
6. Other leading references for this compound class are the following: (a) Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond; Stütz, A. E. (Ed.); Wiley-VCH: New York, 1999;
7. (b) Asano, N.; Molyneux Fleet, G. W. J. Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application. Tetrahedron: Asymmetry 2000, 11, 1645-1680;
8. (c) Martin, O. R.; Compain, P. Design, synthesis and biological evaluation of iminosugar-based glycosyltransferase inhibitors. Curr. Top. Med. Chem 2003, 3, 541.
9. Examples that do not employ tartaric acid: (a) Ono, M.; Tanikawa, S.; Suzuki, K.; Akita, H. Formal synthesis of (-)-anisomycin based on stereoselective nucleophilic substitution along with 1,2-aryl migration. Tetrahedron 2004, 60, 10187;
10. (b) Kang, S. H.; Choi, H-W. Asymmetric amidation of (2S,3S) -pent-4-ene-1,2,3-triol: Total syntheses of (-)-anisomycin and (+)-polyoxamic acid. Chem. Commun. 1996, 1521-1522;
11. (c) Reddy, J. S.; Kumar, A. R.; Rao, B. V. A new approach to (+)-anisomycin. Tetrahedron: Asymmetry 2005, 16, 3154;
12. (d) Kim, J. H.; Curtis-Long, M. J.; Seo, W. D.; Ryu, Y. B.; Yang, M. S.; Park, K. H. Novel and versatile synthesis of pyrrolidine type azasugars, DAB-1 and LAB-1, potent glucosidase inhibitors. J. Org. Chem. 2005, 70, 4082. For more, see Ref. [1].
13. Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Enantioselective catalysis, 4: Synthesis of N-substituted (R,R)-3,4-bis- (diphenylphosphino)pyrrolidines - The use of rhodium complexes for the asymmetric hydrogenation of α-(acylamino) acrylic acid derivatives. Chem. Ber. 1986, 119, 3326-3343.
14. Marson, C. M.; Melling, R. C. Enantioselective syntheses of trans-3,4-difluoropyrrolidines and investigation of their applications in catalytic asymmetric synthesis. J. Org. Chem. 2005, 70, 9771-9779.
15. McCaig, E. A.; Meldrum, K. P.; Wightman, R. H. Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine. Tetrahedron 1998, 54, 9429-9446.
16. Iida, H.; Yamazaki, N.; Kibayashi, C. Highly selective total synthesis of enantiomerically pure (-)-anisomycin. J. Org. Chem. 1986, 51, 1069-1073.
17. Berens, U.; Leckel, D.; Oepen, S. C. Transacetalization of diethyl tartrate with acetals of alpha-dicarbonyl compounds: A simple access to a new class of C-2-symmetric auxiliaries and ligands. J. Org. Chem. 1995, 60, 8204-8208.
18. (a) Ley, S. V.; Polara, A. A fascination with 1,2-diacetals. J. Org. Chem. 2007, 72, 5943-59 and references cited therein.
19. A Specific example is (b) Burke, A. J.; Maycock, C. D.; Ventura, M. R. (+)-O-methylpiscidic acid dimethyl ester. Org. Biomol. Chem. 2006, 4, 2361-2363.
20. Barros, M. T.; Burke, A. J.; Maycock, C. D. The alkylation of a novel acetal derived from (2R,3R)-(+)-tartaric acid: An unexpected rearrangement. Tetrahedron Lett. 1999, 40, 1583-1586.
21. Barros, M. T.; Burke, A. J.; Lou, J.-D.; Maycock, C. D.; Wahnon, J. R. Highly stereoselective aldol reaction for the synthesis of γ-lactones starting from tartaric acid. J. Org. Chem. 2004, 69, 7847-7850.
22. 2-symmetric ligands with 1,4-dioxane backbone derived from tartrates: Syntheses and applications in asymmetric hydrogenation. J. Org. Chem. 2002, 67, 7618-7623.
23. 2 (1,4-diamine)] catalyst. Org. Lett. 2005, 7, 1449-1451;
24. (b) Hems, W. P.; Grasa, G. A. Catalysts. WO 2005/007662 A2, File date, July 7, 2004.
25. Villalgordo, J. M.; Linden, A.; Heimgartner, H. A novel amination reaction with diphenyl phosphorazidate: Synthesis of α-amino-acid derivatives. Helv. Chim. Acta 1996, 79, 213-219.
26. Thompson, A. S.; Hartner, F. W. Jr.; Grabowski, E. J. J. Ethyl (R)-2-azidopropionate. Org. Syn. Coll. 2004, 10, 382-385.
27. Mash, E. A.; Nelson, K. A.; Van Deusen, S.; Hemperly, S. B. 1,4-di-O-alkyl threitols from tartaric acid: 1,4-di-O-benzyl-L- threitol. Org. Synth. 1993, 8, 155-166.
28. Martins, J. G.; Burke, A. J. Unpublished results, 2005.
29. Staudinger, H.; Meyer, J. Über neue organische phosphorverbindungen III: Phosphinmethylenderivate und phosphinimine. Helv. Chim. Acta. 1919, 2, 635-646.
30. Fluka catalogue 2007/2008; Buchs SG, Switzerland, p. 245.
31. Carballo, J. L.; Hernández-Inda, Z.; Pérez, P.; García-Grávalos, M. D. A comparison between two brine shrimp assays to detect in vitro cytotoxicity in marine natural products. BMC Biotech. 2002, 2, 17-21, and references cited therein.
32. Burke, A. J.; Barralus, P. C.; Pereira, A. M. D. R. L. Unpublished results, 2007.
33. Molyneux, P. The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin J. Sci. Technol. 2004, 26, 211-219, and references cited therein.