N-methyl-2-pyrrolidone → (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-ol

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Reaction Conditions

Reaction Steps

In a microwave tube, (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 38) (0.15 g, 0.42 mmol), Na2S (0.20 g, 2.6 mmol) and NMP (3 mL) were placed. The tube was sealed and subjected to microwave heating at 180° C. for 1 h. The reaction was cooled to room temperature, diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-ol (Compound No. 39) (0.06 g, 43%) as a colourless solid. 1H NMR (CDCl3): δ 6.15 (d, 1H), 6.00 (d, 1H), 4.93 (s, 1H), 4.27 (m, 1H), 3.97 (t, 1H), 3.68 (s, 3H), 3.00 (m, 1H), 1.75-1.40 (m, 8H), 1.37 (s, 3H), 1.20-0.93 (m, 2H), 0.92 (s, 3H), 0.90 (m, 1H) 0.68 (s, 3H), 0.62 (s, 3H). MS m/z 345 (C22H32O3+H+).

Provenance & Evidence