Stereoselective synthesis of bicyclic lactones by annelation with functionalised orthoesters

Chemical Communications

Volumn , Issue 11, 2006, Pages 1200-1202

  Maulide, Nuno ^a   Markó, István E ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; FURAN DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33644768294     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b600677a     Document Type: Article

References (27)

1. H. D. Fischer, N. H. Fischer, R. W. Franck and E. J. Olivier, Progress in the Chemistry of Organic Natural Products, vol. 38; Springer-Verlag, Vienna, p. 47
2. H. Krawczyk M. Sliwinski W. M. Wolf R. Bodalski Synlett 1995
3. G. C. Paddon-Jones C. S. P. McErlean P. Hayes C. J. Moore W. A. Konig W. J. Kitching J. Org. Chem. 66 7487
4. R. J. Madhushaw C.-L. Li K.-H. Shen C.-C. Hu R.-S. Liu J. Am. Chem. Soc. 123 7427
5. B. B. Snider B. Shi C. A. Quickley Tetrahedron 56 10127
6. N. Gathergood K. Anker Jorgensen Chem. Commun. 18 1869
7. G. Casiraghi G. Rassu Synthesis 607
8. S. K. Bur S. F. Martin Tetrahedron 57 3211
9. I. E. Markó A. Ates Synlett 1033
10. I. E. Markó J.-C. Vanherck A. Ates B. Tinant J.-P. Leclercq Tetrahedron Lett. 44 3333
11. N. Maulide J.-C. Vanherck I. E. Markó Eur. J. Org. Chem. 19 3962
12. C. Huart L. Ghosez Angew. Chem., Int. Ed. Engl. 36 634
13. P. Ding L. Ghosez Tetrahedron 58 1565
14. M. Asaoka N. Sugimura H. Takei Bull. Chem. Soc. Jpn. 52 1953
15. A. Pelter R. Al-Bayati W. Lewis Tetrahedron Lett. 23 353
16. A. Pelter R. Al-Bayati P. Pardasani Tetrahedron Lett. 27 749
17. A. Pelter R. I. H. Al-Bayati M. T. Ayoub W. Lewis P. Pardasani R. Hansel J. Chem. Soc., Perkin Trans. 1 4 717
18. S. H. Wagner I. J. Lundt J. Chem. Soc., Perkin Trans. 1 780 788
19. G. A. Molander D. J. St. Jean, Jr. J. Org. Chem. 67 3861
20. J. Robichaud F. Tremblay Org. Lett. 10.1021/ol0527328
21. In stark contrast, orthoesters 6c and 6e do not provide similar adducts when reacted with silyl enol ethers derived from cyclic ketones
22. C. Chatgilialoglu Acc. Chem. Res. 25 188
23. J.-W. Huang C.-D. Chen M.-K. Leung Tetrahedron Lett. 40 8647
24. J. M. Andres E. M. Munoz R. Pedrosa A. Perez-Encabo Eur. J. Org. Chem. 17 3387
25. E. J. Corey N. Raju Tetrahedron Lett. 24 5571
26. Interestingly, inspection of product 8d reveals it to be the opposite regioisomer of a formal [2 + 2] cycloaddition of ketene to a dihydrofuran derivative
27. The envelope-like topology of these bicyclic systems directs the hydrogen delivery to the intermediate cyclic radical from the less congested convex-face. Similarly, methylation occurs from the least hindered, exocyclic face