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. Author manuscript; available in PMC: 2017 Apr 27.
Published in final edited form as: J Am Chem Soc. 2016 Apr 12;138(16):5426–5432. doi: 10.1021/jacs.6b02276

Scheme 1. Synthesis of the Carboxylic Acid 10a.

Scheme 1

aReagents and conditions: (a) (S)-hex-5-en-2-amine hydrogen chloride (8), 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (EDC·HCl), hydroxybenzotriazole (HOBT), N,N-diisopropylethylamine (DIPEA), DMF, 23 °C, 84%; (b) HCl, CH2Cl2–1,4-dioxane (7:1), 23 °C, >99%; (c) myristoyl chloride, triethylamine (Et3N), DMF, 23 °C, 82%; (d) RuCl3, NaIO4, H2O–EtOAc–CH3CN (3:2:2), 50 °C, 95%.