Scheme 12.

Classical derivatization strategies of phenylketone fragments. A Derivatization of carbonyl. Common conditions: a NaBH₄/alcohol b Zn-Hg/HCl (Wolff-Kishner reduction) or NH₂NH₂/base/ high temperature (Clemmensen reduction) or HS(CH₂)₃SH/BF₃·Et₂O or NaBH₄/TFA (Gribble reduction for R = aryl) c NH₄OAc/NaBH₃CN/alcohol d R¹NH₂ e Pd/H₂ or Zn/H⁺ f NaBH₄/alcohol g R¹NH₂/NaBH₄/Lewis acid h R¹COCH R²R³ i CH₂R¹R² (R¹,R² = elctron withdrawing group) j Ph₃P = CR¹R² (Wittig reaction) or (OEt)₂POCHR¹R² (Wittig–Horner reaction) k TMSCN/Lewis acid l NHR¹R²/(EtO)₂POCN m H₂O n R¹MgBr or R¹Li o peroxy acid; B Derivatization of acetophenone fragments. Common conditions: a halogenating reagents b nucleophile c R¹X, base d R¹CHO, base e R¹CHO, NHR²R³ f CH₃I/base/Δ g HCHO, base h oxalic acid i RCOOEt, base j PBr₃