Water → HCID 90388631, compound

Participants

Reaction Steps

To a solution of compound 45 (45 mg, 0.16 mmol) in DMSO (3 mL) was added trimethylsulfonium iodide (202 mg, 1.0 mmol) and potassium tert-butoxide (112 mg, 1.0 mmol) at room temperature. After 3 h, water was added (20 mL) 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 46 (35 mg, 75%) as a white solid: mp 165-167° C.; [α]D25 +20.0 (c 0.12, CHCl3); 1H NMR (CDCl3) δ 4.08 (s, 1H), 2.90 (d, J=15.2 Hz, 1H), 2.60 (d, J=15.2 Hz, 1H), 0.87 (s, 3H); 13C NMR (CDCl3) δ 70.5, 66.5, 53.6, 48.3, 47.2, 47.0, 42.1, 40.4, 40.2, 37.9, 36.2, 34.2, 34.0, 32.8, 29.0, 28.8, 25.8, 23.3, 14.3; IR νmax 3418, 1443, 1378, 851 cm−1. MS (FAB) for [C19H30O2]+: 290.2246. Found: 290.2243.

Provenance & Evidence