Reaction Steps
This compound was prepared from 5,5-dimethylcyclohex-2-en-1-one (11) and 2-(tert-butyl)dimethylsilyloxybenzyl bromide (9) in three steps in the manner previously described for the synthesis of olefin 16, affording the desired phenol as a colorless oil. 1H NMR (400MHz, CDCl3) δ0.90 and 1.15 (2s, 2×3H, geminal-CH3 's), 1.85 and 2.24 (d of ABq, 2H, JAB =18.8 Hz, JA =5,5 Hz, JB =0 Hz, 4-H), 2.06 (dd, 1H, J=11.4, 3.2 Hz, 6-H), 3.30 and 2.88 (d of ABq, 2H, JAB =13.5 Hz, JA =11.4 Hz, JB =3.4 Hz, benzylic-CH2), 4.20 and 4.69 (2s, 2×1H, methylidene-CH2), 4.61 (s, 1H, OH), 5.77 (ddd, 1H, J=7.8, 5.4, 5.4 Hz, 3-H), 6.09 (dd, 1H, J=7.5, 2.2 Hz, 2-H), 6.75 (dd, 1H, J=7.1, 0.8 Hz, 3'-H), 6.82 (ddd, 1H, J=8.4, 7.3, 1.1 Hz, 5'-H), 6.97 (dd, 1H, J=5.9, 1.5 Hz, 6'-H), 7.05 ppm (ddd, 1H, J=9.3, 7.8, 1.7 Hz, 4'H). [Compound 34 is hereinafter also referred to as COMPOUND "C" or 120363]
