Efficient total synthesis of piceatannol via (e)-selective wittig-horner reaction

Synthetic Communications

Volumn 39, Issue 8, 2009, Pages 1425-1432

  Young Han, Su ^a   Suck Lee, Hyun ^a   Hye Choi, Da ^a   Woon Hwang, Jung ^a   Mo Yang, Deok ^a   Jun, Jong Gab ^a  

^a Hallym University   (South Korea)

Author keywords

(E) Selective Wittig Horner reaction; piceatannol; polyphenol; stilbene

Indexed keywords

ALDEHYDE; ALPHA RESORCYLIC ACID; PHOSPHONIC ACID DERIVATIVE; PICEATANNOL; SODIUM HYDROXIDE; STILBENE; TETRAHYDROFURAN; TRIPHENYLPHOSPHINE;

ARTICLE; BENZYLATION; BROMINATION; DEALKYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HORNER REACTION; SONOGASHIRA REACTION; STEREOCHEMISTRY;

EID: 67650269612     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802528944     Document Type: Article

References (11)

1. King, F. E.; King, T. J.; Godson, D. H.; Manning, L. C. The chemistry of extractives from hardwoods, part XXVIII: The occurrence of 3:4:3′: 5′- tetrahydroxy- and 3:4:5:3′:5′-pentahydroxy-stilbene in Vouacapoua species. J. Chem. Soc. 1956, 4477-4480.
2. Kimura, Y.; Okuda, H.; Arichi, S. Effects of stilbenes on arachidonate metabolism in leukocytes. Biochim. Biophys. Acta 1985, 834, 275-278.
3. Stivala, L. A.; Savio, M.; Carafoli, F.; Perucca, P.; Bianchi, L.; Maga, G.; Forti, L.; Pagoni, U. M.; Albini, A.; Prosperi, E.; Vannini, V. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. J. Biol. Chem. 2001, 276, 22586-22594.
4. Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K.V.; Thomas, C. F.; Beecher, C. W. W.; Fong, H. H. S.; Farnsworth, N. R.; Farnsworth, A.; Kinghorn, A. D.; Metha, R. G.; Moon, R. C.; Pezzuto, J. M. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997, 275, 218-220.
5. Docherty, J. J.; Fu, M. M. H.; Stiffler, B. S.; Limperos, R. J.; Pokabla, C. M.; DeLucia, A. L. Resveratrol inhibition of herpes simplex virus replication. Antiviral Res. 1999, 43, 135-145.
6. Han, S. Y.; Bang, H. B.; Lee, H. S.; Hwang, J. W.; Choi, D. H.; Yang, D. M.; Jun, J.-G. A new synthesis of stilbene natural product piceatannol. Bull. Korean Chem. Soc. 2008, 29, 1800-1802.
7. Bosanac, T.; Yang, J.; Wilcox, C. S. Precipitons-functional protecting groups to facilitate product separation: Applications in isoxazoline synthesis. Angew. Chem., Int. Ed. 2001, 40, 1875-1879.
8. Botella, L.; Najera, C. Synthesis of methylated resveratrol and analogues by Heck reactions in organic and aqueous solvents. Tetrahedron 2004, 60, 5563-5570.
9. Cho, C.-H.; Park, K. Parallel synthesis of unsymmetrical trans-stilbenes. Bull. Korean Chem. Soc. 2007, 28, 1159-1166.
10. Piao, Z. S.; Wang, L.; Feng, Y. B.; Zhao, Z. Z. Studies on the synthesis of a natural product-piceatannol and its analogs. Chin. Chem. Lett. 2002, 13, 521-524.
11. Drewes, S. E.; Fletcher, L. P. Polyhydroxystilbenes from the heartwood of Schotia brachypetala. J. Chem. Soc., Perkin Trans. 1 1974, 961-962.