Water → HCID 90388277, compound

Participants

Reaction Steps

To a solution of compound 14 (60 mg, 0.23 mmol) in DMSO (3 mL) was added trimethylsulfonium iodide (204 mg, 1.0 mmol) and potassium tert-butoxide (112 mg, 1.0 mmol) at room temperature. After 3 h, water (20 mL) was added and the product extracted into EtOAc (50 mL×3). The combined extracts were dried, filtered and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 30% EtOAc in hexanes) to give compound 15 (48 mg, 72%) as a white solid: 160-162° C.; [α]D20 16.5 (c 0.20, CHCl3); 1H NMR (CDCl3) δ 3.64-3.50 (m, 1H), 2.91 (d, J=4.9 Hz, 1H), 2.62 (d, J=4.9 Hz, 1H), 0.87 (s, 3H); 13C NMR (CDCl3) δ 71.7, 70.6, 53.6, 47.1, 42.0, 40.3, 40.2, 38.9, 38.4, 36.3, 35.7, 31.8, 29.8, 29.6, 28.9 (2×C), 25.8, 25.5, 14.4; IR νmax 3387, 1733 cm−1. Anal. Calcd for (C19H30O2): C, 78.57; H, 10.41. Found: C, 78.36; H, 10.50.

Provenance & Evidence