A concise and diastereoselective total synthesis of cis and trans-pterocarpans

Chemical Communications

Volumn , Issue 21, 2005, Pages 2689-2691

  Jiménez González, Leticia ^a   Álvarez Corral, Míriam ^a   Muñoz Dorado, Manuel ^a   Rodríguez García, Ignacio ^a  

^a UNIVERSITY OF ALMERÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PTEROCARPAN DERIVATIVE;

ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 20844462187     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b500919g     Document Type: Article

References (18)

1. P. M. Dewick, The Flavonoids: Advances in Research Since 1980, ed. J. B. Harborne, Chapman & Hall, London, 1994, pp 166-180.
2. M. Daniel, Handbook of Phytoalexin Metabolism and Action, ed. Marcel Dekker Inc., New York, 1995.
3. T. Maurich, L. Pistelli and G. Turchi, Mutat. Res., 2004, 561, 75.
4. (a) T. A. Engler, K. O. Lynch, J. P. Reddy and G. S. Gregory, Bioorg. Med. Chem. Lett., 1993, 3, 6, 1229;
5. T. A. Engler, K. O. LaTessa, R. Iyengar, W. Chai and K. Agrios, Bioorg. Med. Chem, 1996, 4, 10, 1755.
6. R. Chanphen and Y. Thebtaranonth, J. Nat. Prod, 1998, 61, 9, 1146.
7. A. J. M. Da Silva, A. L. Coelho, A. B. C. Simas, R. A. M. Moraes, D. A. Pinheiro, F. F. A. Fernández, E. Z. Arruda, P. R. R. Costa and P. A. Melo, Bioorg. Med. Chem. Lett., 2004, 14, 2, 431.
8. T. G. van Aardt, H. van Rensburg and D. Ferreira, Tetrahedron, 2001, 57, 33, 7113 and references therein.
9. A. Schöning and W. Friedrichsen, Z. Naturforsch., B. Chem. Sci., 1989, 44, 8, 975.
10. I. R. Baxendale, A. Lee and S. V. Ley, J. Chem. Soc., Perkin Trans 1, 2002, 1850.
11. P. Schwab, R. H. Grubbs and J. W. Ziller, J. Am. Chem. Soc., 1996, 118, 100.
12. M. Scholl, S. Ding, C. W. Lee and R. H. Grubbs, Org. Lett., 1999, 1, 953.
13. 1H-NMR of the reaction crudes. Careful column chromatography was needed to avoid silica promoted protodesilylation
14. 2.
15. J. H. Cassidy, S. P. Marsden and G. Stemp, Synlett. 1997, 1411.
16. C. Meyer and J. Cossy, Tetrahedron Lett, 1997, 38, 45, 7861.
17. S. M. Miles, S. P. Marsden, R. J. Leatherbarrow and W. J. Coates, J. Org. Chem., 2004, 69, 20, 6874.
18. S. M. Miles, S. P. Marsden, R. J. Leatherbarrow and W. J. Coates, Chem. Commun., 2004, 2292-2293.