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. Author manuscript; available in PMC: 2008 Sep 3.
Published in final edited form as: J Med Chem. 2007 May 10;50(11):2622–2639. doi: 10.1021/jm0613323

Scheme 2a.

Scheme 2a

a Reagents and conditions: (a) LiOH·H2O, THF, H2O; dil. HCl. (b) H2NOTHP, DIC, DMAP, CHCl3, 0 °C to room temperature. (c) BBr3, CH2Cl2, −78 °C; H3O+. (d) Tf2O, pyridine, CH2Cl2, 0 °C to room temperature. (e) 16, Pd(PPh3)4, aq K3PO4, DME, reflux. (f) SnCl2•2 H2O, EtOH, reflux. (g) CuBr2, t-BuNO2, MeCN, 0 °C to room temperature. (h) Pd(PPh)3, CuI, Et3N, Me3Si-acetylene, reflux. (i) (n-Bu)4NF, THF. (j) Catecholborane, THF, reflux. (k) MeCOCH2P(Ph)3Br, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, THF, room temperature to 70 °C. (l) H2SeO3, dioxane/H2O (10:1). (m) Tetraethyl methylenediphosphonate, 50% aq NaOH, CH2Cl2. (n) 20% aq HCl, reflux.