Compound 44

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InChIKey SHPMSTNWDJPIHT-GMQQYTKMSA-N

Compound data: CIF

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

Compound 44 was synthesized by the general method outlined for compound 23 replacing starting material 22 for 42. The crude mixture was purified by flash chromatography (silica gel, 5:1 hexanes/EtOAc) and pTLC (5:1 hexanes/EtOAc) to provide 43 (30% yield) and 44 (16% yield). m.p. = 162–164 ºC; HRMS (m/z): calcd for C₂₇H₃₅NO₂SH⁺ [M+H]⁺, 438.2461; found, 438.2469; IR (film) ν_max = 3279, 2959, 1461, 1326, 1160, 1094 cm^-1; [α]_D = +48.1 º (c = 0.21, CH₂Cl₂); ¹H NMR (600 MHz, CDCl₃) δ 7.70 (d, J = 8.2 Hz, 2 H), 7.27 (d, J = 8.2 Hz, 2 H), 7.15 (d, J = 8.1 Hz, 1H), 7.02 (dd, J = 8.1, 1.4 Hz, 1 H), 6.87 (s, 1 H), 5.90 (ddd, J = 10.0, 6.3, 1.7 Hz, 1 H), 5.21 (dd, J = 10.0, 2.8 Hz, 1 H), 4.28 (dd, J = 10.0, 2.2 Hz, 1 H), 3.07 (dd, J = 12.0, 10.2 Hz, 1 H), 2.84 (heptet, J = 7.0 Hz, 1 H), 2.78 (dt, J = 17.0, 3.0 Hz, 1 H), 2.72 – 2.63 (m, 1 H), 2.53 (dd, J = 17.0, 6.3 Hz, 1 H), 2.46 (dd, J = 12.3, 2.7 Hz, 1 H), 2.42 (s, 3 H), 2.10 (d, J = 17.9 Hz, 1 H), 2.05 – 1.99 (m, 1 H), 1.66 – 1.61 (m, 2 H), 1.27 – 1.20 (m, 9 H), 0.92 (s, 3 H); ¹³C NMR (151 MHz, CDCl₃) δ 145.9, 144.5, 143.3, 137.3, 135.3, 132.6, 129.8, 128.9, 127.1, 126.8, 125.8, 124.3, 51.2, 40.9, 39.6, 39.4, 36.5, 33.6, 30.7, 25.5, 24.1, 24.1, 21.6, 19.8, 19.7.