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. Author manuscript; available in PMC: 2018 Apr 12.
Published in final edited form as: ChemMedChem. 2017 Nov 24;12(23):1942–1952. doi: 10.1002/cmdc.201700614

Scheme 1.

Scheme 1

Reagents and conditions: a) K2CO3, MeOH, 23°C, 1 h, 98%; b) NaClO2, cis-2-methyl-2-butene, NaH2PO4. H2O, tBuOH-H2O, 23°C, 50 min, 95%; c) TFA, CH2Cl2, 23°C, 3 h; d) 6, N,N-DIPEA, MeCN/H2O, 23°C, 3 days 89% (over two steps); e) pyridine, Boc2O, (NH4)2CO3, THF, 23 °C, 14 h, 76%; f) iBuOCOCl, NMM then MeNHOMe·HCl, dry CH2Cl2, −15°C →23°C, 12 h, 76%; g) TFA, CH2Cl2, 23 °C, 2 h; h) 6, N,N-DIPEA, MeCN,23°C, 5 days, 73–78%; i) MeMgBr (3 M in Et2O), dry THF, −78°C, 4 h, 98%; j) RuCl[(R,R)-TsDPEN](mesitylene) for 3e or RuCl(p-cymene)[(S,S)-Ts-DPEN] for 3f, TEA, HCOOH, dry CH2Cl2, 0°C →23°C, 7 h, 94–98 %.