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. Author manuscript; available in PMC: 2022 Jun 2.
Published in final edited form as: J Am Chem Soc. 2021 May 20;143(21):8193–8207. doi: 10.1021/jacs.1c03572

Scheme 3.

Scheme 3.

Syntheses of six-membered ring analogs 12–15

Reagents and conditions: (a) AgOC(O)CF3, CH3NO2, 0 °C – r.t., 16h; then NH3/MeOH, 1 h; (b) DMP, CH3CN, NaHCO3 (b) NaH, DMF; PMBCl, 0 °C – r.t., 16h; (c) CHF2PO(OEt)2, tBuLi (1.7 M in pentane), −100 °C – r.t., 2h; then reflux, 16h; (d) CAN, CH3CN, H2O, 0 °C - r.t., 10 h; (e) HCl (aq. 4 M), 75 °C, 5h. (e) 2-PySO2CF2H, tBuOK, DMF −60 °C, then −40 °C, 2h, NH4Cl (saturated aq.), HCl (3M), overnight; (f) PhSeCl, KHMDS (1M in THF), −78 °C – r.t., 3h; (g) Boc2O, DIPEA, DMAP, DCM, r.t., overnight; (h) K2CO3, EtOH, 0 °C - r.t. 3h; (i) m-CPBA, DCM, r.t., 3h; (j) HCl (aq. 4 M), AcOH, 80 °C, overnight.