Total Synthesis of (+)- and (−)-Ononitol

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• 2 mp 182–185°C, [α]D = −21° (c 2.3, CHCl3), HRMS(Cl) mz 581.3657, calc. 581.3690; NMR δH (CDCl3) 0.84(s, 3H), 0.95(s, 3H), 0.98(s, 3H), 1.18(s, 9H), 1.19(s, 9H), 1.24(s, 9H), 1.37–1.43(m, 2H), 1.68–1.86(m, 5H), 3.47(s, 3H), 3.72 (dd, J = 7.6 9.1 Hz, 1H), 4.00 (dd, J = 5.7 6.7 Hz, 1H), 4.46(dd, J = 4.0 5.7 Hz, 1H), 4.95(dd, J = 7.6 8.2 Hz, 1H), 5.11(dd, J = 9.1 4.0 Hz, 1H), 5.16(dd, J = 6.7 8.2 Hz, 1H) ppm; δC (C6D6) 10.46, 21.19(2C), 28.00(9C), 30.34, 39.49, 39.51, 46.03, 46.19, 48.79(2C), 52.65, 60.71, 72.12, 72.49, 74.19, 74.50, 74.74, 80.13, 118.96, 177.32, 177.40, 177.93 ppm.
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• 3 mp 139–141°C (from heptane - CH2Cl2 4:1); [α]D = +14.3° (c 2.1, CHCl3); NMR δH (CDCl3) 0.86(s, 3H), 0.87(s, 3H), 1.00(s, 3H), 1.24–1.51(m, 3H), 1.65–2.06(m, 4H), 3.34(t, J = 7.3 Hz, 1H), 3.39(t, J = 7.4 Hz, 1H), 3.60(s, 3H), 3.37–3.93(m, 3H), 4.29(dd, J = 6.3 4.2 Hz, 1H) ppm; δC (C6D6) 10.83, 21.10, 21.49, 28.04, 30.86, 45.12, 46.26, 48.92, 52.50, 60.10, 70.97, 75.32, 75.68, 76.05, 77.48, 85.18, 118.48 ppm.
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• (+)-ononitol: mp 168–169° [lit.20 172°C, lit.21 167–168°C], [α]D = +5.5° (c 2.2, H2O) [lit.20 + 6.6°, lit.21 +5.5°]; NMR δH (D2O) 3.34(t, J = 6.8 Hz, 1H), 3.35 (dd, J = 2.8 9.1 Hz, 1H), 3.47(dd, J = 2.8 9.9 Hz, 1H), 3.58(s, 3H), 3.56–3.93(m, 2H), 4.00(t, J = 2.9 Hz, 1H) ppm; δC (CD3OD) 61.01, 73.05, 73.26, 74.22, 74.36, 76.13, 84.55 ppm.
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• (-)-ononitol: mp 168–169°C; [α]D = −5.7° (c 2.0, H2O).
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