Asymmetric total synthesis of rugulactone, an α-pyrone from Cryptocarya rugulosa

Synthesis

Volumn , Issue 16, 2010, Pages 2787-2793

  Allais, Florent ^a   Aouhansou, Mahoulo ^a   Majira, Amel ^a   Ducrot, Paul Henri ^a  

^a INSTITUT JEAN PIERRE BOURGIN   (France)

Author keywords

Metathesis; Natural products; Olefination; Pyrones; Total synthesis

Indexed keywords

ASYMMETRIC SYNTHESIS; ASYMMETRIC TOTAL SYNTHESIS; CHIRAL POOL; COUPLING REACTION; CROSS METATHESIS; DEPROTECTION; E-OLEFIN; INTRAMOLECULAR LACTONIZATION; NATURAL PRODUCTS; OLEFINATION; ONE POT; TOTAL SYNTHESIS; UNSATURATED ESTERS;

ESTERS; OLEFINS; STEREOCHEMISTRY;

SYNTHESIS (CHEMICAL);

2 PYRONE DERIVATIVE; ALKENE; ESTER DERIVATIVE; LACTONE; RUGULACTONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CROSS COUPLING REACTION; CRYPTOCARYA; CRYPTOCARYA RUGULOSA; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; LACTONIZATION; OLEFINATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 77955376517     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218836     Document Type: Article

References (33)

1. Meragelman T L., Scudiero D A., Davis R E., Staudt L M., McCloud T G., Cardellina J H. II., Shoemaker R H., J. Nat. Prod. 2009 72 336
2. Gilmore T D., Oncogene 2006 25 6680
3. Brasier A R., Cardiovasc. Toxicol. 2006 6 111
4. Perkins N D., Nat. Rev. Mol. Cell Biol. 2007 8 49
5. Gilmore T D., Oncogene 1999 18 6842
6. Tian B, Brasier A R., Recent Prog. Horm. Res. 2003 58 95
7. Albensi B C., Mattson M P., Synapse (Hoboken, NJ, U. S.) 2000 35 151
8. Karin M, Cell Res. 2008 18 334
9. Pikarsky E, Ben-Neriah Y, Eur. J. Cancer 2006 42 779
10. Mantovani A, Marchesi F, Portal C, Allavena P, Sica A, Adv. Exp. Med. Biol. 2008 610 112
11. Rali T, Wossa S W., Leach D N., Molecules 2007 12 149
12. Toribio A, Bonfils A, Delannay E, Prost E, Harakat D, Henon E, Richard B, Litaudon M, Nuzillard J.-M, Renault J.-H, Org. Lett. 2006 8 3825
13. Davies-Coleman M T., Rivett D E. A., Prog. Chem. Org. Nat. Prod. 1989 55 1
14. Cavalheiro A J., Yoshida M, Phytochemistry (Elsevier) 2000 53 811
15. Murga J, García-Fortanet J, Carda M, Marco J A., J. Org. Chem. 2004 69 7277; and references therein
16. Maxwell A, Dabideen D, Reynolds W F., McLean S, J. Nat. Prod. 1998 61 815
17. Reddipalli G, Venkataiah M, Fadnavis N W., Tetrahedron: Asymmetry 2010 21 320
18. Mohapatra D K., Das P P., Reddy D S., Yadav J S., Tetrahedron Lett. 2009 50 5941
19. KumarReddy D, Shekhar V, SrikhanthReddy T, PurushothamReddy S, Venkateswarlu Y, Tetrahedron: Asymmetry 2009 20 2315
20. Allais F, Ducrot P.-H, Synthesis 2010 1649
21. Allais F, Martinet S, Ducrot P.-H, Synthesis 2009 3571
22. Quentin M, Allasia V, Pegard A, Allais F, Ducrot P.-H, Favery B, Levis C, Martinet S, Masur C, Ponchet M, Roby D, Schlaich N.-L, Jouanin L, Keller H, PLoS Pathog. 2009 5 e1000264
23. Li D.-R, Khang D.-H, Sun C.-Y, Zhang J.-W, Yang L, Chen J, Liu B, Su C, Zhou X.-S, Lin G.-Q, Chem. Eur. J. 2006 12 1185
24. Xiangshu X, Donghu B, Synlett 2001 535
25. Gaunt M J., Jessiman A S., Orsini P, Tanner H R., Hook D F., Ley S V., Org. Lett. 2003 5 4819
26. Grubbs R H., Chang S, Tetrahedron 1998 54 4413
27. As the first pathway did not operate as predicted, compound 12 was not thoroughly characterized. Compound 13 was identified among other products in the crude mixture and was not purified.
28. Bressy C, Allais F, Cossy J, Synlett 2006 3455
29. Yokokawa F, Asano T, Shioiri T, Tetrahedron 2001 57 6311
30. Jin M, Taylor R E., Org. Lett. 2005 7 1303
31. Fürstner A, Seidel G, Kindler N, Tetrahedron 1999 55 8215
32. Still W C., Gennari C, Tetrahedron Lett. 1983 24 4405
33. Karuturi R, Vangaru S, Jondoss J P. S., ChitturiBhujanga R, Yenamandra V, Helv. Chim. Acta 2009 92 1866