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. 2008 Jun 11;73(13):4949–4955. doi: 10.1021/jo800545r

Scheme 5. Synthesis of Fragment 29.

Scheme 5

Reagents and conditions: (a) Ag2O, MeI (solvent) 86%; (b) DIBAL-H, THF, −78 °C; (c) 1,3-propanedithiol, BF3·OEt2, CH2Cl2, 28 °C, 86% from lactone 21; (d) (COCl)2, DMSO, i-Pr2NEt, −78 °C, 98%; (e) 25, Mg, 1,2-dibromoethane, Et2O, −78 °C, 85%; (f) TESCl, ImH, CH2Cl2, 28 °C; (g) I2, CH2Cl2, 0 °C, 90% from 26; (h) MeI (xs), K2CO3, MeCN/pH 7 buffer (4:1), 28 °C, 92%.