HCID 67003850, compound → HCID 16720388, compound

Participants

Reaction Steps

In a manner similar to the synthesis of 107, compound 119 (350 mg, 0.611 mmol) was treated with zinc (<10 micron, 397 mg, 6.11 mmol) to afford 108 as an amorphous solid (207 mg, 97%). Rf=0.45 (toluene/ethyl acetate, 3/1, v/v); [α]25D=−2.5° (c=1.0, CHCl3); 1H NMR (300 MHz, CDCl3): δ 7.34-7.26 (m, 5H, aromatic), 4.57 (s, 2H, CH2Ph), 3.87 (m, 1H, H-3), 2.64 (dd, 1H, J2a,2b=15.6 Hz, J2a,3=6.9 Hz, H-2a), 2.55 (dd, 1H, J2a,2b=15.6 Hz, J2b,3=5.1 Hz, H-2b), 1.68-1.38 (m, 3H, H-4, H-15), 1.26-1.14 [m, 20H, H-(5-14)], 0.86 (d, 6H, J15,16=6.9 Hz, H-16); 13C NMR (75 MHz, CDCl3): δ 176.95 (C═O), 138.08-127.71 (aromatic), 75.71 (C-3), 71.53 (CH2Ph), 39.47 (C-2), 39.05 (C-12), 34.12 (C-4), 22.65 (C-14). HR MS (m/z) calculated for C24H40O3 [M+Na]+, 399.2870. found, 399.2552.

Provenance & Evidence