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. 2018 Aug 1;140(34):10839–10847. doi: 10.1021/jacs.8b05465

Scheme 2. Synthesis of the Closed Form of 13,14-Dimethylcethrene.

Scheme 2

Reaction conditions: (a) methyl acrylate (MA), Pd(OAc)2, PPh3, K2CO3, Bu4NBr, DMF, 110 °C, 20 h; (b) H2, Pd/C, CH2Cl2/EtOH, room temperature, 3 h; (c) LiI, 2,4,6-collidine, 185 °C, 3 h; (d) (COCl)2, 65 °C, 2.5 h; (e) AlCl3, CH2Cl2, −78 to −10 °C, 5 h; (f) NaBH4, CH2Cl2/EtOH, room temperature, 1.5 h; (g) p-TSA, toluene, 90 °C, 5 min; (h) p-chloranil, C6H6, room temperature, 16 h.