First total synthesis of 5(S)-hydroxyrecifeiolide

References

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• FT-IR (neat) 3550, 3427, 2931, 2860, 1734, 1624 1448, 1370, 1236, 1052, 983 cm−1; [α]25D (c 0.10, +28.0) 1H-NMR (400 MHz, CDCl3) δ ppm 5.38–5.28 (m, 2H), 5.18 (m, 1H), 3.76 (tt, 1H, J = 9.6, 3.8 Hz), 2.41 (m, 1H), 2.34–2.25 (m, 2H, overlapped), 2.21 (m, 1H), 2.14–1.99 (m, 2H, overlapped), 1.86–1.77 (m, 3H), 1.68 (m, 1H, overlapped), 1.48 (m, 1H), 1.24 (d, 3H, J = 6.3 Hz), 1.17 (m, 1H); (400 MHz, DMSO-d6) δ ppm 5.31–5.21 (m, 1H,), 5.17–5.07 (m, 1H,), 5.01 (dtd, 1H, J = 6.35, 12.7, 15.65 Hz), 4.26 (br S, 1H), 3.56–3.46 (m, 1H), 2.32–2.22 (m, 2H), 2.20–2.12 (m, 1H), 2.1–2.05 (m, 1H, overlapped), 2.02–1.86 (m, 2H, overlapped), 1.72–1.6 (m, 2H), 1.58–1.5 (m, 1H) 1.46–1.37 (m, 1H), 1.36–1.27 (m, 1H), 1.15 (d, 3H, J = 6.3 Hz), 1.03–0.93 (m, 1H) 13C-NMR (100 MHz, CDCl3) δ ppm 173.1, 132.5, 127.3, 68.4, 67.6, 40.9, 34.2, 32.2, 30.3, 28.1, 20.4, 20.1; (100 MHz, DMSO-d6) δ ppm 172.2, 132.7, 126.7, 67.8, 65.3, 40.3, 33.8, 32.8, 30.0, 27.7, 20.2, 19.9; ESIMS m/z = 235 (M + Na)+ HRMS m/z = 235 (M + Na)+ calcd 235.1310, found 235.1329 for C12H20O3Na.
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