A New Deoxygenation Method for Taxanes Using Hypophosphorous Acid
被引量：1
A New Deoxygenation Method for Taxanes Using Hypophosphorous Acid
摘要
An efficient and practical radical chain deoxygenation method by phosphorus centered radicals generated from hypophosphorous acid was developed in the synthesis of analogues of paclitaxel.
参考文献9
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7[7]Selected data of 14-deoxy-SIA: white solid, [α]+54 (c 0.83, CHCl3); mp: 128.5-131.2℃; 1H NMR (500MHz, CDCl3, δ ppm): 6.06 (dd,1H, J=5.3Hz,12.3Hz, H-10), 5.38 (dd,1H, J=2Hz, 6.3Hz, H-2), 5.27(t, 1H, J=3Hz, H-5), 5.25 (s, 1H, H-20), 4.89 (s, 1H, H-20), 3.08(d,1H, J=6Hz, H-3), 2.45 (m, 1H, H-13), 2.37 (dd, 1H, J=12Hz, 14.5Hz, H-9), 2.12 (s, 3H, OAc-CH3-10), 2.06 (s, 3H, CH3-18), 2.04 (s, 3H, OAc-CH3-2), 2.03 (s, 3H, OAc-CH3-4), 2.09-1.87 (m 3H, H-7, H-13, H-14), 1.80 (m, 3H, H-1, 2×H-6), 1.68 (m, 1H, H-14), 1.59 (s, 3H, CH3-16), 1.58 (m, 1H, H-9), 1.22(m, 1H, H-7),1.05 (s, 3H, CH3-17), 0.85 (s, 3H, CH3-19); 13CNMR (125MHz, CDCl3, δ ppm): 170.18 (OAc-C=O), 169.63 (OAc-C=O), 169.62 (OAc-C=O), 144.35 (C-4), 136.96 (C-12), 133.90 (C-11), 116.36 (C-20), 78.73 (C-5), 72.25 (C-2), 70.49 (C-10), 52.01 (C-1), 43.78 (C-9), 41.19 (C-3), 39.68 (C-8), 37.09 (C-15), 33.65 (C-7), 31.67 (C-17), 30.10 (C-13), 28.96 (C-6), 25.33 (C-16), 22.50 (19-CH3), 22.01 (OAc-CH3), 21.66 (OAc-CH3), 21.65 (OAc-CH3), 21.22 (18-CH3), 18.29 (C-14); FABMS: m/z 447.3(M+1).
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8[8]Selected data of compound 3: white solid, [α]+83 (c 0.54, CHCl3); mp 198-200℃; 1HNMR(500MHz, CDCl3, δ ppm): 7.97(dt, 2H, J=7.7Hz, 1.5Hz, Bz), 7.58(t, 1H, J=7.5Hz, Bz), 7.46(t, 2H, J=7.5Hz, Bz), 6.00(dd, 1H, J=12.3Hz, 5.5Hz, H-10), 5.77(dd, 1H, J=5.7Hz, 2.5Hz, H-2), 4.75(dd, 1H, J=9.2Hz, 3.0Hz, H-5), 4.31(d, 1H, J=8.0Hz, H-20), 4.16(d, 1H, J=8.0Hz, H-20), 2.47(dd, 1H, J=14.5Hz, 12.5Hz, H-9), 2.42(m, 1H, H-13), 2.26(d, 1H, J=6Hz, H-3), 2.11(m, 2H, H-6, H-13), 2.06(s, 3H, OAc-CH3-10), 1.97(m, 1H, H-6), 1.90(s, 3H,CH3-18), 1.86(m, 1H, H-1), 1.67(s, 3H, CH3-16), 1.63(m, 1H, H-7), 1.33(s, 3H, CH3-19), 1.07(s, 3H, CH3-17); 13C NMR (125MHz, CDCl3, δ ppm): 170.12(10-OAc-C=O), 165.34(2-Bz-C=O), 137.81(C-12), 134.43(C-11),133.34, 129.58, 129.48, 128.65(6xph), 87.56(C-5), 80.52(C-4), 76.24(C-20), 73.43(C-10), 70.50(C-2), 50.23(C-1), 46.01(C-9), 44.85(C-3), 37.21(C-8), 36.51(C-15), 35.03(C-17), 32.35(C-13), 29.60(C-7), 27.22(C-6), 25.12(C-16), 21.76(C-19), 21.51 (OAc-CH3), 21.13(C-18), 18.18(C-14); FABMS: m/z 483.4(M+1).
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9[9]Reaction procedure: The solution of compound 1 , triethyl amine(5eq), 50% hypophosphorous acid(5eq) and cyclohexene(5eq) in dioxane under argon was treated with AIBN(0.1eq) solution ( 0.1 mol/L in dioxane) for several times ( at every 30 min) under reflux. The solution was washed with water and dried over anhydrous NaSO4, concentrated and chromatographed to give 14-deoxy-SIA.
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