Review Article
A Review on Platensimycin: A Selective FabF Inhibitor
Scheme 10
Synthesis of tetracyclic cage. (i) PhI(O2CCF3)2, OHCH2CH2OH, MeCN, 0°C, 2 h. (ii) (S)-BINAP, [Rh(cod)2]BF4, C7H8, H2O, Et3N, CH3-CH(BF3K)=CH2. (iii) (1) NaBH4, MeOH, (2) MEMCl, -Pr2NEt, CH2Cl2, (3) TsOH, Me2CO, 0°C, (4) i-Bu2AIH, CH2Cl2, 0°C, (5) Et3SiH, (CF3CO)2O, CH2Cl2, −20°C. (iv) PhSH, Cs2CO3, DMF, D 170°. (v) (1) i-Pr3SiCl, imidazole, CH2Cl2, 23°C, 12 h and (2) Br2, CH2Cl2, −78°C. (vi) n-Bu4NF, THF, D 130°C. (vii) [Rh(cod)2]BF4, (R,R)-DIOP, H2 600 psi, CH2Cl2, 16 h. (viii) (1) TMSOTf, Me3N, CH2Cl2 and (2) IBX, MPO, DMSO.