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. 2010 Jul 15;1(8):416–421. doi: 10.1021/ml100118k

Scheme 2. Synthesis of Carbacycle 7.

Scheme 2

Reagents and conditions: (i) TBAF, THF, 40 °C, 1 h (93%). (ii) TPAP, NMO, DCM, 1 h (quant.). (iii) Propargyl alcohol OTBDPS, BuLi, −78 °C, 1 h (90%). (iv) H2, Lindlar's catalyst, quinoline, AcOEt, 1 h (80%). (v) MEMCl, DIPEA, DCM, 40 °C, 12 h (75%). (vi) DDQ, phosphate buffer, pH 7.2, 1 h (97%). (vii) TBAF, THF, 40 °C, 1 h (quant.). (viii) TPAP, NMO, DCM, 1 h (quant.). (ix) TiCl4, Zn dust, pyridine, THF, 1 h (49%). (x) (AcO)2O, Et3N, DMAP, DCM, 30 min (quant.).