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. 2014 Aug 15;19(8):12368–12420. doi: 10.3390/molecules190812368

Scheme 2.

Solid-phase synthesis of AM-toxin II (2) by Horikawa.

Scheme 2

Reagents and conditions: (a) o-NO2-C6H4-SeCN, Bu3P/pyridine, rt, 2 h (83%); (b) Zn, AcOH/THF, rt, 2 h (82%); (c) succinic anhydride, DIPEA/CH2Cl2, rt, 3 h, (81%); (d) Gly-Wang resin, HATU, DIPEA/DMF, vortex, rt, overnight, (98% in Kaiser test); (e) Pd(PPh3)4, dimedone/THF, vortex, rt, 3 h; (f) NaNO2/AcOH aq., 30 min, (76%); (g) Cs2CO3, then allyl bromide, rt, overnight, (65%); (h) Boc-Ala, DCC, DMAP/DMF, rt, overnight (73%); (i) cat. Pd(PPh3)4, piperidine/THF, rt, 2 h, (93%); (j) l-App-OAll, HATU/DIPEA/DMF, rt, 6 h (88%); (k) 50% TFA/CH2Cl2, rt, 1 h (99%); (l) HATU, DIPEA/DMF, vortex, rt, overnight; (m) cat. Pd(PPh3)4, dimedone/THF, vortex, rt, 2 h; (n) 40% piperidine/DMF, vortex, rt, 1 h; (o) FDPP (pentafluorophenyl diphenylphosphinate), DIPEA/DMF, vortex, rt, 2 d; (p) TBHP (tert-butyl hydroperoxide)/CH2Cl2-TFE, vortex, rt, 7 h.