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. Author manuscript; available in PMC: 2008 Dec 12.
Published in final edited form as: J Am Chem Soc. 2007 Nov 14;129(49):15279–15294. doi: 10.1021/ja074725f

Scheme 2.

Scheme 2

Synthesis of compound 3.

Reagents and conditions: (a) 11, EDC, HOBt, N,N-diisopropylethylamine, CH2Cl2, overnight, 91%; (b) i. 4 N HCl in 1,4-dioxane, MeOH; ii. Boc-N-methyl-L-alanine, EDC, HOBt, N,N-diisopropylethylamine, CH2Cl2, 86% over two steps; (c) i. azidomethylbenzene, CuSO4, (+)-sodium -L-ascorbate, tert-butanol - H2O 2:1; ii. 4 N HCl in 1,4-dioxane, MeOH, 74% over two steps.