HCID 67776369, compound → HCID 67774119, compound

Participants

Reaction Steps

To a solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,13aR,13bR)-methyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate (4 g, 8.50 mmol) in CH2Cl2 (100 mL) was added PCC (5.50 g, 25.5 mmol). The reaction mixture was stirred for 15 hours at room temperature. TLC indicated starting material was consumed and a new compound was generated. The reaction mixture was concentrated under reduced pressure and the residue was purified by biotage using ethyl acetate/hexanes (0-20%) to give the desired product (1R,3aS,5aR,5bR,7aR,11aR,13aR,13bR)-methyl 5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate as a white solid (4 g, 100%). 1H NMR (500 MHz, DMSO-D6) δ ppm 0.85 (s, 3H), 0.88 (s, 3H), 0.93 (s, 3H), 0.95 (s, 3H), 0.98 (s, 3H), 1.00-1.64 (m, 17H), 1.65 (s, 3H), 1.73-1.84 (m, 3H), 2.07-2.23 (m, 2H), 2.28-2.39 (m, 1H), 2.39-2.48 (m, 1H), 2.86-3.00 (m, 1H), 3.56-3.63 (s, 3H), 4.58 (s, 1H), 4.71 (d, J=1.83 Hz, 1H).

Provenance & Evidence