Compound 22

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

Prepared according to the general procedure outlined for compound 13 using (E)-N-(3,7-dimethylocta-2,6-dien-1-yl)-4-methyl-N-(4- oxobutyl)benzenesulfonamide. Purified by flash chromatography (1% Et₂O/CH₂Cl₂) to provide the title compound (91 mg, 81% yield, 11:11:1:1 dr, 94% ee) as a colorless oil. Analytical data: [α]_D²¹-43.4 (c = 1.00, CHCl₃); ¹H NMR (500 MHz, CDCl₃): δ 9.52 (d, J = 3.3 Hz, 1H), 9.49 (d, J = 3.3 Hz, 1H), 7.62 (d, J = 8.0 Hz, 4H), 7.32 (d, J = 8.1 Hz, 4H), 5.07-5.01 (m, 2H), 3.57 (m, 2H), 3.44 (d, J = 11.7 Hz, 2H), 2.50-2.45 (m, 2H), 2.43 (s, 6H), 2.40-2.34 (m, 2H), 2.30-2.22 (m, 2H), 2.04-1.94 (m, 5H), 1.88-1.75 (m, 5H), 1.68 (d, J = 7.5 Hz 6H), 1.65-1.61 (m, 2H), 1.59 (d, J = 9.6 Hz 6H), 1.43-1.35 (m, 2H), 1.30-1.23 (m, 1H), 1.04-0.98 (m, 1H), 0.96 (d, J = 6.9 Hz, 3H), 0.83 (d, J = 6.9 Hz, 3H); ¹³C NMR (125 MHz, CDCl₃): δ 203.2, 143.7, 133.0, 132.0, 129.7, 127.6, 123.8, 49.7, 49.4, 46.1, 45.2, 44.8, 44.8, 40.8, 39.3, 34.8, 32.9, 32.5, 25.8, 25.6, 24.5, 24.4, 21.5, 17.7, 17.3, 14.7; HRMS (ESI⁺) Calcd. for C₂₁H₃₁NO₃S+H, 378.2097; Found, 378.2098; IR (thin film, cm^-1) 2970, 2923, 2856, 1727, 1597, 1444, 1351, 1217, 1162, 1092, 1039, 927, 815, 751, 712, 658; TLC (60:40 hexanes:EtOAc): R_f= 0.65. HPLC analysis of the corresponding alcohol (AD, 20% iPrOH/hexane, 1.0 mL/min, 220 nm) indicates 94% ee: t_R= 8.1, 8.9, 12.3, 16.7 min.