(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-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-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 titled compound was prepared in 86.6% yield following the method described in step 1 for the preparation of Example 1 described above, using (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-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. MS: m/e 543.5 (M−16)+, 2.87 min. 1H NMR (400 MHz, CHLOROFORM-d) δ 5.84-5.72 (m, 1H), 5.47-5.32 (m, 1H), 4.72 (s, 1H), 4.59 (s, 1H), 4.24-3.99 (m, 2H), 3.09-2.74 (m, 1H), 2.67-2.40 (m, 3H), 2.26-2.10 (m, 1H), 2.09-1.92 (m, 3H), 1.69 (s, 3H), 1.67-1.65 (m, 1H), 1.64-1.31 (m, 9H), 1.29-1.22 (m, 5H), 1.17-1.05 (m, 4H), 1.02 (s, 6H), 0.98-0.93 (m, 7H), 0.82 (m, 3H).

Provenance & Evidence