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. 2021 Jan 13;6(3):2284–2311. doi: 10.1021/acsomega.0c05589

Scheme 2. General Synthetic Routes for the Synthesis of Compounds 22–30 and 35.

Scheme 2

Reagents and conditions: (i) EtOH, AcOH, reflux, and 1–18 h; (ii) spiro[isochromane-1,4′-piperidine], AcOH, DCM, then NaBH(OAc)3, and 18 h; (iii) EtOH, H2O, 35 °C, and 18 h; (iv) SOCl2, pyridine, 50 °C, 2 h then ethanolamine, DCM, rt, 3 h, then SOCl2, rt, and 18 h; (v) NaH, THF, 0 °C, and 3 h; (vi) DIBAL, DCM, −78 °C—rt, then MnO2, DCM, rt, and 48 h; (vii) spiro[isochromane-1,4′-piperidine], AcOH, DCM, then NaBH(OAc)3, 18 h; and (viii) 3 M HCl, 100 °C, and 18 h.