HCID 54397734, compound → HCID 9820546, compound

Participants

Reaction Steps

The above ethyl ester 19 (37 mg, 0.09 mmol) in 2 mL MeOH was hydrolyzed as described for Example 1 to give the crude acid. The crude mixture was purified by HPLC (82% MeOH/18% 10 mmol NH4OAc+0.3% AcOH) to give 18 mg (55%) of pure (2E, 4E)-6-[1-(6-t-butyl-1,1-dimethyl-indan-4-yl)-cyclopropyl]-3-methyl-2,4-hexadienoic acid (20). 1H NMR (400 MHz, CDCl3) δ7.05 (d, J=1.5 Hz, 1H, aromatic), 7.02 (d, J=1.7 Hz, 1H, aromatic), 6.09 (dt, J=15.7 and 7.2 Hz, 1H, vinylic CH), 5.97 (d, J=15.7 Hz, 1H, vinylic CH), 5.66 (s, 1H, vinylic CH), 2.90 (t, J=7.2 Hz, 2H, allylic CH2), 2.34 (d, J=7.2 Hz, 2H, allylic CH2), 2.22 (s, 3H, aliphatic CH3), 1.91 (t, J=7.0 Hz, 2H, aliphatic CH2), 1.30 (s, 9H, aliphatic 3CH3), 1.25 (s, 6H, aliphatic 2CH3), 0.80 (dd, J=10.1, 6.2 Hz, 2H, aliphatic CH2), 0.71 (dd, J=10.2, 3.9 Hz, 2H, aliphatic CH2).

Provenance & Evidence