Scheme 2.

Synthesis of Deuterated 2B

Reagents: (a) TBDMSCl, imidazole, 56.4%; (b) (i) 1-bromo-[²H₉]-butane (3B), Mg⁰, THF (ii) CuCl₂, LiCl, NMP, 98.3%; (c) TBAF, 99.1%; (d) Bobbitt’s salt, SiO₂, 75.6%; (e) SnCl₂, ethyl diazoacetate, 80.6%; (f) NaBH₄, 79.7%; (g) LiOH, 89.3% (h) (i) 10, NHS, EDC, DMAP (ii) Pd/C, H₂, 78.2%; (i) TBAF, 85.1% (j) LiOH, 73%; (k) 13-methylpentadecanoic acid, EDC, DMAP, 79.6%; (l) TBAF, 85.1% (m) KOSi(CH)₃, 58%.