Compound 23a

((1R,2S,4S,5R)-2-((R)-Hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium-1-yl)((((R)-1,1,1-trichloro-4-(hex-5-yn-1-ylamino)-4-oxobutan-2-yl)oxy)sulfonyl)amide

From: Simultaneous structure–activity studies and arming of natural products by C–H amination reveal cellular targets of eupalmerin acetate

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InChIKey CNZNTQKYYIHABH-JDKVGPOUSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Compound 23a was prepared following the general procedure shown for Compound 13a synthesis. (19% yield). m.p. = 152.6 oC. 1H NMR (500 MHz, CDCl3) δ 8.93 (d, J = 5.0 Hz, 1H), 8.29 (d, J = 8.5 Hz, 1H), 8.14 (d, J = 8.5 Hz, 1H), 7.76 (t, J = 7.5 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.65 (t, J = 7.5 Hz, 1H), 6.99 (br s, 1H), 6.13 (br s, 1H), 5.56 (ddd, J = 18.0, 11.0, 6.5 Hz, 1H), 5.42 (t, J = 4.5 Hz, 1H), 5.05 (d, J = 18.0 Hz, 1H), 5.02 (d, J = 11.0 Hz, 1H), 4.65-4.59 (m, 2H), 4.25-4.21 (m, 1H), 3.99 (br s, 1H), 3.70 (t, J = 9.0 Hz, 1H), 3.51-3.48 (m, 1H), 3.29-3.22 (m, 2H), 3.21-3.14 (m, 1H), 3.01 (dd, J = 15.5, 4.5 Hz, 1H), 2.82 (br s, 1H), 2.35-2.22 (m, 2H), 2.12 (t, J = 6.5 Hz, 2H), 2.11 (br s, 1H), 2.05-1.96 (m, 1H), 1.90 (br s, 1H), 1.62-1.55 (m, 2H), 1.51-1.45 (m, 3H); 13C NMR (125 MHz, CDCl3) δ 169.2, 150.1, 148.1, 146.1, 137.0, 130.3, 129.6, 127.6, 124.7, 123.1, 118.9, 117.2, 99.8, 83.96, 83.94, 73.2, 68.7, 67.3, 64.9, 55.3, 39.9, 39.5, 39.4, 28.2, 26.5, 26.3, 25.6, 20.7, 18.0; HRMS (MALDI+): m/z calcd. for C29H35Cl3N4O5SNa [M+Na] 679.1285, found 679.1274.

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