Reaction Steps
By chromatographing the mixture of cis and trans isomers of CS-8 on a (S)-N-(1-naphthyl)leucine chiral stationary phase packed into a MPLC column, which chiral stationary phase is described by Pirkle, Deming and Burke in Chirality, 3:183-187 (1991) the contents of which are incorporated herein by reference, 2.68 g of enantiomerically pure cis CS-8, i.e., (cis)-6,7-Dimethyl-4-[N-(3,5-dinitrobenzoyl)]amino-3-(10-undecenyl)-1,2,3,4-tetrahydrophenanthrene, (last eluted enantiomer) was obtained, as were samples of the trans form of CS-8 (the first eluted enantiomer). Physical data for cis CS-8, obtained as a yellowish solid, were as follows: mp 181°-182° C., 1H NMR (CDCl3) δ 1.19-1.39 (m, 14H), 1.42-1.77 (m, 3H), 1.96-2.07 (m, 4H), 2.36 (s, 3H), 2.40 (s, 3H), 3.03-3.10 (m, 2H), 4.89-5.03 (m, 2H), 5.74-5.88 (m, 1H), 6.08 (dd, J=9.2 Hz, J=2.8 Hz, 1H), 6.20 (d, J=9.2 Hz, 1H), 7.16 (d, J=8.2 Hz, 1H), 7.52 (s, 1H), 7.61 (d, J=8.2 Hz, 1H), 7.85 (s, 1H), 8.84 (d, J=1.7 Hz, 2H), 9.08 (t, J=1.7 Hz, 1H), IR (KBr) CM-1 3440, 2920, 2850, 1680, 1650, 1540, 1500, exact (EI) mass. calcd. for C34H41N3 O5 : 571.3046, Found: 571.3046, [α]D20 -126.2(c 091, CH2Cl2).
