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Synthetic pathway to tetrahydro-1H-inden-2,6-dione 5 and derivatives.
(a) (i) LDA, THF, –78 °C; (ii) MeI, –78 °C, 2 h (96%); (b) (i) LDA, DMPU, THF, –78 °C; (ii) 8, –78 °C; 3 h (84%); (c) t-BuLi, KH, THF, –78 °C, 45 min; (d) n-Bu4NH2PO4, EtOH, 75 °C, 12 h (68% from 2a); (e) KOH, EtOH, rt, 16 h (89%); (f) O3, CH2Cl2, –78 °C (73%); (g) HO(CH2)2OH, TsOH, toluene, reflux, 2 h (92%); (h) H2, Pd/C, EtOAc, rt, 2.5 h (100%).
