HCID 67003850, compound → HCID 86644998, compound

Participants

Reaction Steps

In a manner similar to the synthesis of 107, compound 120 (500 mg, 0.666 mmol) was treated with zinc (<10 micron, 430 mg, 6.66 mmol) to afford 109 as an amorphous solid (335 mg, 96%). Rf=0.35 (toluene/ethyl acetate, 4/1, v/v); [α]25D=−0.6° (c=1.0, CHCl3); 1H NMR (300 MHz, CDCl3): δ 5.19 (m, 1H, H-3), 2.58 (m, 2H, H-2), 2.25 (t, 2H, J=7.5 Hz, H-2′), 1.60-1.43 (m, 5H, H-4, H-15, H-3′), 1.23-1.14 [m, 44H, H-(5-14), H-(4′-15′)], 0.85-0.83 (m, 9H, H-16, H-16′); 13C NMR (75 MHz, CDCl3): δ 176.24 (C═O), 173.27 (C═O), 69.95 (C-3). HR MS (m/z) calculated for C33H64O4 [M+Na]+, 547.4697. found, 547.5009.

Provenance & Evidence