Acetone → HCID 86648184, compound

Participants

Reaction Conditions

Reaction Steps

(3aS,4R,6aR)-2,2-dimethyl-6-(trityl oxymethyl)-4-vinyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (1-3) (1.4 g, 3.19 mmol, 1.0 equiv) was dissolved in a freshly prepared solution of DMDO (dimethyl dioxirane) in acetone (37.7 mL, 0.076 M, 0.9 equiv). The resulting mixture was stirred at 0° C. for 4 hours, then concentrated and purified via flash chromatography on silica gel column (ethyl acetate/hexanes) to yield (3aS,4S,6aR)-2,2-dimethyl-4-((S)-oxiran-2-yl)-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (1-5). 1H NMR (500 MHz, CDCl3) δ 7.21-7.47 (m, 15H), 5.83 (2 s, 1H), 4.99 (t, 1H, J=5 Hz), 4.63 (t, 1H, J=5 Hz), 3.86 (d, 1H, J=14 Hz), 3.67 (d, 1H, J=14 Hz), 2.85-2.97 (m, 2H), 2.77 (m, 1H), 2.60 (m, 1H), 1.35 (s, 3H), 1.32 (s, 3H).

Provenance & Evidence