A Review on Platensimycin: A Selective FabF Inhibitor

Scheme 12

Synthesis of tetracyclic cage. (i) CH₂Cl₂, −78°C, 14 h, (ii) LDA, THF, −78°C, then PhNO, −78°C, 2 h, and then LiOH dioxane/H₂O 30°C, 20 h, (iii) H₂O₂/NaOH Et₂O/H₂O 0°C to r.t., 45 min, (iv) CuBr·Me₂S, CH₂CMgBr THF/Me₂S, −40°C to r.t., (v) 4.5 mol% HNTf₂, CH₂ClCH₂Cl, 70°C, 45 min, (vi) DIBAL-H, toluene, −78°C, 30 min, then Et₂AlCN BF₃·OET₂, 20 min, (vii) DIBAL-H/n-BuLi, −78°C to 0°C, 25 min, (viii) NaH, CH₃COCH₂P(O)(OET)₂, THF, 0°C, 20 min, (ix) 2.02 eq NaIO₄, 3.5 mol% RuCl₃ 6 : 1 CH₃CN/H₂O r.t., 3 h, and (x) 1 eq pyrrolidine-2-carboxylic acid, DMF, r.t., 5 days, then 2N NaOH(aq) 0°C to r.t., 40 min.