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Enantio Selective Synthesis of New Phenylpropanoid: Isolated from Walsura trifoliata
Corresponding Author(s) : B. Nageswara Rao
Asian Journal of Chemistry,
Vol. 31 No. 9 (2019): Vol 31 Issue 9
Abstract
A new phenylpropanoid containing flavon-3-ol has been isolated from the leaves of traditional medicinal plant, Walsura trifoliata. The structure of the compound was established on the basis of spectroscopic evidence [2D NMR, HREIMS] and by its alternative synthesis. The synthesis of this natural product was achieved from inexpensive and readily available starting materials of phloroglucinol dihydrate. Key reaction sequence includes Grubbs-II RCM reaction, Wittig reaction and sharpless dihydroxylation using AD-mix α.
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- H. Fujiki, M. Suganuma, K. Imai and K. Nakachi, Cancer Lett., 188, 9 (2002); https://doi.org/10.1016/S0304-3835(02)00379-8.
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References
H. Fujiki, M. Suganuma, K. Imai and K. Nakachi, Cancer Lett., 188, 9 (2002); https://doi.org/10.1016/S0304-3835(02)00379-8.
M. Monagas, M. Urpi-Sarda, F. Sánchez-Patán, R. Llorach, I. Garrido, C. Gómez-Cordovés, C. Andres-Lacueva and B. Bartolomé, Food Funct., 1, 233 (2010); https://doi.org/10.1039/c0fo00132e.
A. Takagaki, S. Otani and F. Nanjo, Biosci. Biotechnol. Biochem., 75, 582 (2011); https://doi.org/10.1271/bbb.100683.
A. Takagaki and F. Nanjo, J. Agric. Food Chem., 63, 8262 (2015); https://doi.org/10.1021/acs.jafc.5b03676.
L.M.V. Tillekeratne, A. Sherette, P. Grossman, L. Hupe, D. Hupe and R.A. Hudson, Bioorg. Med. Chem. Lett., 11, 2763 (2001); https://doi.org/10.1016/S0960-894X(01)00577-7.
N. Salah, N.J. Miller, G. Paganga, L. Tijburg, G.P. Bolwell and C. RiceEvans, Arch. Biochem. Biophys., 322, 339 (1995); https://doi.org/10.1006/abbi.1995.1473.
A.H. Wu, C.C. Tseng, D. Van Den Berg and M.C. Yu, Cancer Res., 63, 7526 (2003).
W. Tang, H. Hioki, K. Harada, M. Kubo and Y. Fukuyama, J. Nat. Prod., 70, 2010 (2007); https://doi.org/10.1021/np0703895.
B. Wungsintaweekul, K. Umehara, T. Miyase and H. Noguchi, Phytochemistry, 72, 495 (2011); https://doi.org/10.1016/j.phytochem.2010.12.018.
R. Saijo, G. Nonaka and I. Nishioka, Chem. Pharm. Bull. (Tokyo), 37, 2063 (1989); https://doi.org/10.1248/cpb.37.2063.
K.M. Ch Appa Rao, B.N. Rao, L.V. Ramana, and M.S. Appa Rao, J. Pharmacog. Phytochem., 6, 1314 (2017).
V.P. Vitullo and N.J. Grossman, J. Am. Chem. Soc., 94, 3844 (1972); https://doi.org/10.1021/ja00766a030.
S. Awale, Y. Tezuka, S. Wang and S. Kadota, Org. Lett., 4, 1707 (2002); https://doi.org/10.1021/ol020042n.
J.C. Anderson, C. Headley, P.D. Stapleton and P.W. Taylor, Tetrahedron, 61, 7703 (2005); https://doi.org/10.1016/j.tet.2005.05.086.
D. Forget-Champagne, M. Mondon, N. Fonteneau and J.-P. Gesson, Tetrahedron Lett., 42, 7229 (2001); https://doi.org/10.1016/S0040-4039(01)01376-4.
S.B. Wan, D. Chen, Q.P. Dou and T.H. Chan, Bioorg. Med. Chem., 12, 3521 (2004); https://doi.org/10.1016/j.bmc.2004.04.033.