An Efficient Method for C8-Prenylation of Flavonols and Flavanones

Tomoyuki Kawamura; Moemi Hayashi; Rie Mukai; Junji Terao; Hisao Nemoto

doi:10.1055/s-0031-1290756

Synthesis, Table of Contents

Synthesis 2012; 44(9): 1308-1314
DOI: 10.1055/s-0031-1290756

paper

An Efficient Method for C8-Prenylation of Flavonols and Flavanones

Tomoyuki Kawamura

^aDepartment of Pharmaceutical Chemistry, Institute of Health Biosciences, Graduate School of The University of Tokushima, 1-78-1, Sho-machi, Tokushima 770-8505, Japan, Fax: +81(88)6337284 Email: nem@ph.tokushima-u.ac.jp

,

Moemi Hayashi

^aDepartment of Pharmaceutical Chemistry, Institute of Health Biosciences, Graduate School of The University of Tokushima, 1-78-1, Sho-machi, Tokushima 770-8505, Japan, Fax: +81(88)6337284 Email: nem@ph.tokushima-u.ac.jp

,

Rie Mukai

^bDepartment of Nutrition and Biosciences, Institute of Health Biosciences, Graduate School of the University of Tokushima, 3-18-15, Kuramoto-cho, Tokushima, 770-8503, Japan

,

Junji Terao

^bDepartment of Nutrition and Biosciences, Institute of Health Biosciences, Graduate School of the University of Tokushima, 3-18-15, Kuramoto-cho, Tokushima, 770-8503, Japan

,

Hisao Nemoto*

^aDepartment of Pharmaceutical Chemistry, Institute of Health Biosciences, Graduate School of The University of Tokushima, 1-78-1, Sho-machi, Tokushima 770-8505, Japan, Fax: +81(88)6337284 Email: nem@ph.tokushima-u.ac.jp

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Abstract

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Abstract

Synthesis of C8-prenylated flavonols and flavanones via the palladium-catalyzed 7-O-1,1-dimethylprop-2-enylation, followed by Claisen rearrangement is described. Two regioselectivities (carbon–carbon bond formation at either the tail or head of the prenyl group and carbon–carbon bond formation at either C8 or C6) were efficiently improved when acetic anhydride was used as a solvent instead of N,N-dimethylformamide.

Key words

flavonoid - Claisen rearrangement - prenylation - Kaiho’s method - flavonols - flavanones

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References

References

1a Harborne JB, Baxter H. The Handbook of Natural Flavonoids . Vols. 1 and 2. John Wiley & Sons; Chichester: 1999
1b Harborne JB. The Flavonoids: Advances in Research since 1986 . Chapman and Hall; London: 1994
1c Harborne JB. The Flavonoids: Advances in Research since 1980 . Chapman and Hall; London: 1988
1d Harborne JB, Mabry TJ. The Flavonoids: Advances in Research . Chapman and Hall; London: 1982
1e Harborne JB, Mabry TJ, Mabry H. The Flavonoids . Chapman and Hall; London: 1975

2a Yazaki K, Sasaki K, Tsurumaru Y. Phytochemistry 2009; 70: 1739
2b Nomura T. Yakugaku Zasshi 2001; 121: 535
2c Ren Y, Kardono LB. S, Riswan S, Chai H, Farnsworth NR, Soejarto DD, Carcache-Blanco EJ, Kinghorn AD. J. Nat. Prod. 2010; 73: 949
2d Huang Y.-C, Hwang T.-L, Chang C.-S, Yang Y.-L, Shen C.-N, Liao W.-Y, Chen S.-C, Liaw C.-C. J. Nat. Prod. 2009; 72: 1273
2e Tabopda TK, Ngoupayo J, Awoussong PK, Mitaine-Offer A.-C, Ali MS, Ngadjui BT, Lacaille-Dubois M.-A. J. Nat. Prod. 2008; 71: 2068
2f Meragelman KM, MacKee TC, Boyd MR. J. Nat. Prod. 2001; 64: 546
2g Conseil G, Decottignies A, Jault J.-M, Comte G, Barron D, Goffeau A, Pietro AD. Biochemistry 2000; 39: 6910
2h Jia SS, Ma CM, Wang JM. Acta. Pharm. Sin. 1990; 25: 758
2i Fukai T, Wang Q.-H, Takayama M, Nomura T. Heterocycles 1990; 31: 373

3 Wong SP, Shen P, Lee L, Li J, Yong EL. J. Pharm. Biomed. Anal. 2009; 50: 216

4a Wäetjen W, Weber N, Lou Y.-J, Wang Z.-Q, Chovolou Y, Kampkötter A, Kahl R, Proksh P. Food Chem. Toxicol. 2007; 45: 119
4b Ahmed-Belkacem A, Pozza A, Muñoz-Martínez F, Bates SE, Castanys S, Gamarro F, Pietro AD, Pérez-Victria JM. Cancer Res. 2005; 65: 4852
4c Sohn H.-Y, Son KH, Kwon C.-S, Kwon G.-S, Kang SS. Phytomedicine 2004; 11: 666
4d Comte G, Daskiewicz J.-B, Bayet C, Conseil G, Viornery-Vanier A, Dumontet C, Pietro AD, Barron D. J. Med. Chem. 2001; 44: 763

5a Daskiewicz J.-B, Depeint F, Viornery L, Bayet C, Comte-Sarrazin G, Comte G, Gee JM, Johnson IT, Ndjoko K, Hostettmann K, Barron D. J. Med. Chem. 2005; 48: 2790
5b Dong X, Fan Y, Yu L, Hu Y. Arch. Pharm. Chem. Life Sci. 2007; 372
5c Gester S, Metz P, Zierau O, Vollmer G. Tetrahedron 2001; 57: 1015

6a Kaiho T, Miyamoto M, Nobori T, Katakami T. Yuki Gosei Kagaku Kyokaishi 2004; 62: 27
6b Kaiho T, Yokoyama T, Mori H, Fujiwara J, Nobori T, Odaka H, Kamiya J, Maruyama M, Sugawara T. JP 6,128,238, 1994
6c Tang J, Qian K, Zhang B.-N, Chen Y, Xia P, Yu D, Xia Y, Yang Z.-Y, Chen C.-H, Morris-Natschke LS, Lee K.-H. Bioorg. Med. Chem. 2010; 18: 4363
6d Li N.-G, Wang J.-X, Liu X.-R, Lin C.-J, You Q.-D, Guo Q.-L. Tetrahedron Lett. 2007; 48: 6586
6e Tisdale EJ, Chowdhury C, Vong BG, Li H, Theodorakis EA. Org. Lett. 2002; 4: 909

7 Tisdale EJ, Slobodov I, Theodorakis EA. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 12030

8a Picq M, Prigent AF, Nemoz G, Andre AC, Pacheco H. J. Med. Chem. 1982; 25: 1192
8b Jurd L. J. Am. Chem. Soc. 1958; 80: 5531
8c Jurd L. J. Org. Chem. 1962; 27: 1294
8d Peña-Montes C, Lange S, Castro-Ochoa D, Ruiz-Noria K, Cruz-García F, Schmid R, Navarro-Ocaña A, Earrés A. J. Mol. Catal. B: Enzym. 2009; 61: 225
8e Tischer S, Metz P. Adv. Synth. Catal. 2007; 349: 147

9a Al-Maharik N, Botting NP. Eur. J. Org. Chem. 2008; 5622
9b Li M, Han X, Yu B. J. Org. Chem. 2003; 68: 6842

10 Jiang H, Hamada Y. Org. Biomol. Chem. 2009; 7: 4173
11 Ramesh C, Mahender G, Ravindraneth N, Das B. Tetrahedron 2003; 59: 1049