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. Author manuscript; available in PMC: 2021 Oct 13.
Published in final edited form as: Chembiochem. 2014 Aug 22;15(14):2087–2096. doi: 10.1002/cbic.201402042

Scheme 2.

Scheme 2.

Synthesis of 2 via B-alkyl Suzuki coupling and Liebeskind-Srogl coupling. Detailed reaction conditions and reagents: a) 3,4-dihydro-2H-pyran, p-TsOH, THF, rt, 24 h; b) LiAlH4, THF, reflux, 30 min; c) Dess-Martin periodinane, NaHCO3, CH2Cl2, rt, 1h; d) Ph3P+CH3Br‒, n-BuLi, THF, −78 °C, 1 h; e) 9-BBN, PhMe/THF (1:1), 85 °C, 20 min; f) 1-bromo-4-iodobenzene, Pd(dppf)Cl2∙CH2Cl2, 3 M aqueous NaOH solution, 85 °C, 1 h; g) Pd2(dba)3, DavePhos, bis(pinacolato)diboron, KOAc, 1,4-dioxane, microwave heating at 110 °C, 30 min; h) NaIO4, HCl, THF/H2O (4:1), rt, overnight; i) 14, CuTC, Pd2(dba)3, TFP, THF, microwave heating at 100 °C, 30 min.