(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate → ethyl 3-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)bicyclo[3.1.0]hex-2-ene-6-carboxylate

Participants

Reaction Steps

The title compound was prepared following the method described in step 1 for the preparation of Example 1, using (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate and ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bicyclo[3.1.0]hex-2-ene 6-carboxylate as the reactants. The title compound was obtained as a mixture of diastereomers in 54% yield. MS: m/e 721.55 (M+H)+, 2.901 min (method 8). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.81 (dd, J=6.3, 1.5 Hz, 1H), 5.50-5.37 (m, 1H), 4.72 (d, J=2.0 Hz, 1H), 4.60 (d, J=0.8 Hz, 1H), 4.19-4.05 (m, 3H), 3.11-3.00 (m, 7H), 2.97-2.82 (m, 1H), 2.74-2.43 (m, 6H), 2.17 (td, J=6.6, 3.1 Hz, 1H), 2.09-2.01 (m, 2H), 2.00-1.73 (m, 3H), 1.70 (s, 3H), 1.66-1.18 (m, 20H), 1.16-1.01 (m, 11H), 0.97 (m, 3H), 0.83 (m, 3H).

Provenance & Evidence