Diastereoselective synthesis of enantiopure γ-butenolide- butyrolactones towards Pseudopterogorgia lactone furanocembranoid substructures

Synlett

Volumn 23, Issue 20, 2012, Pages 2909-2912

  MacAbeo, Allan Patrick G ^a,b   Lehmann, Christian W ^c   Reiser, Oliver ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF SANTO TOMAS   (Philippines)

^c MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

asymmetric synthesis; furans; lactones; marine furanocembranoids; vinylogous Mukaiyama addition

Indexed keywords

2 [3' [1,3]DIOXOLAN 2 YL 2 METHOXY 3 METHYL 5' OXO 2',3',4',5' TETRAHYDRO 2H [2,2']BIFURANYL YLIDENEMETHYL]ACRYLIC ACID ETHYL ESTER; 2 [3' [1,3]DIOXOLAN 2 YL 3 METHYL 5' OXO 2',3',4',5' TETRAHYDRO[2,2']BIFURANYL 5 YLMETHYL]ACRYLIC ACID ETHYL ESTER; 3 [1,3]DIOXOLAN 2 YL 3' METHYL 3,4 DIHYDRO 2H,2'H [2,2']BIFURANYL 5,5' DIONE; BUTENOLIDE; CYCLOPROPYLCARBALDEHYDE; DITERPENOID; GAMMA BUTENOLIDE BUTYROLACTONE; GAMMA BUTYROLACTONE; GAMMA BUTYROLACTONE DERIVATIVE; GAMMA LACTONE DERIVATIVE; GAMMA LACTONE GAMMA BUTENOLIDE; LACTONE; LEWIS ACID; SILOXYFURANE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; LACTONIZATION; PSEUDOPTEROGORGIA; SYNTHESIS;

EID: 84868702264     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317555     Document Type: Article

References (35)

1. Marrero J., Rodriguez A. D., Baran P., Raptis R. G., Sanchez J. A., Orteg-Barria E., Capson T. L. Org. Lett.: 2004; 6 1661
2. Rodriguez A. D., Shi Y.-P. J. Org. Chem.: 2000; 65 5389
3. Marrero J., Benitez J., Rodriguez A. D., Zhao H., Raptis R. G. J. Nat. Prod.: 2008; 71 381
4. Doroh B., Sulikowski G. A. Org. Lett.: 2006; 8 903
5. Miao R., Gramani S. G., Lear M. J. Tetrahedron Lett.: 2009; 50 1731
6. Nicolau K. C., Adsool V. A., Hale C. R. H. Angew. Chem. Int. Ed.: 2011; 50 5149
7. Macabeo A. P. G, Kreuzer A., Reiser O. Org. Biomol. Chem.: 2011; 9 3146
8. Farcet J. P., Himmelbauer M., Mulzer J. Org. Lett.: 2012; 14 2195
9. Li Y., Pattenden G., Rogers J. Tetrahedron Lett.: 2010; 51 1280
10. Kimbrough T. J., Roethle P. A., Mayer P., Trauner D. Angew. Chem. Int. Ed.: 2010; 49 2619
11. Roethle P. A., Trauner D. Nat. Prod. Rep.: 2008; 25 298
12. Böhm C., Schinnerl M., Bubert C., Zabel M., Labahn T., Parisini E., Reiser O. Eur. J. Org. Chem.: 2000; 2955
13. Böhm C., Reiser O. Org. Lett.: 2001; 3 1315
14. Bandichhor R., Nosse B., Sörgel S., Böhm C., Seitz M., Reiser O. Chem.-Eur. J.: 2003; 9 1
15. Schinnerl M., Böhm C., Seitz M., Reiser O. Tetrahedron: Asymmetry: 2003; 14 765
16. Kalidindi K., Jeong W. B., Schall A., Bandichhor R., Nosse B., Reiser O. Angew. Chem. Int. Ed.: 2007; 46 6361
17. Casiraghi G., Zanardi F., Appendino G., Rassu G. Chem. Rev.: 2000; 100 1929
18. Denmark S. E., Heemstra J. R. Jr, Beutner G. L. Angew. Chem. Int. Ed.: 2005; 44 4682;
19. Angew. Chem. 2005, 117, 4760.
20. Kalesse M. Top. Curr. Chem.: 2005; 244 43
21. Hosokawa S., Tatsuta K. Mini-Rev. Org. Chem.: 2008; 5 1
22. Zanardi F., Battistini L., Curti C., Casiraghi G. Chemtracts: 2010; 123
23. Otera J., Dan-oh N., Nozaki H. J. Org. Chem.: 1991; 56 5307
24. Orita A., Sakamoto K., Hamada Y., Mitsutome A., Otera J. Tetrahedron: 1999; 55 2899
25. Gawronski J. K., Chen Q. H., Geng Z., Huang B., Martin M. R., Mateo A. I., Brzotowska M., Rychilewska U., Feringa B. L. Chirality: 1997; 9 537
26. Gawrosnki J. K., van Oeveren A., van der Deen H., Leung C. W., Feringa B. L. J. Org. Chem.: 1996; 61 1513
27. Zanardi F., Battistini L., Rassu G., Pinna L., Mor M., Culeddu N., Casiraghi G. J. Org. Chem.: 1998; 63 1368
28. Jefford C. W., Jaggi D., Boukouvalas J. Tetrahedron Lett.: 1987; 28 4037
29. Figadere B., Chaboche C., Peyrat J. F., Cave A. Tetrahedron Lett.: 1993; 34 8093
30. Zanardi F., Battistini L., Rassu G., Auzzas L., Pinna L., Marzocchi L., Acquotti D., Casiraghi G. J. Org. Chem.: 2000; 65 2048
31. Kamel H. N., Ferreira D., Garcia-Fernandez L. F., Slattery M. J. Nat. Prod.: 2007; 70 1223
32. Venkateswarlu Y., Sridevi K. V., Rama Rao M. J. Nat. Prod.: 1999; 62 756
33. Epifánio R.deA, Maria L. F., Fenical W. J. Braz. Chem. Soc.: 2000; 11 584
34. Sánchez M. C., Ortega M. J., Zubia E., Carballo J. L. J. Nat. Prod.: 2006; 69 1749
35. Grote D., Dahse H.-M, Seifert K. Chem. Biodiversity: 2008; 5 2449