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. Author manuscript; available in PMC: 2018 Aug 28.
Published in final edited form as: Angew Chem Int Ed Engl. 2017 Jul 28;56(36):10900–10904. doi: 10.1002/anie.201705924

Scheme 5.

Scheme 5

Synthesis of 12-desmethyl herboxidiene: a) 1-Trimethylsilyl-1-propyne, THF, −78 °C, then K2CO3, MeOH, 95%; b) Cp2Zr(H)Cl, CH2Cl2, then Me2Zn, then 26, then NaOMe, 64%; c) Re2O7•SiO2, CH2Cl2, 67%; d) tBuOOH, VO(acac)2, CH2Cl2, −15 °C, 38%, 48% brsm; e) K2CO3, H2O, MeOH, reflux, 85%.