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

Scheme 8. Synthesis of Apoptolidinone D.

Scheme 8

Reagents and conditions: (a) 34, 1-propenyl pinacol boronic ester (10 equiv), PhMe, 80 °C, 6 h then 40 °C, 24 h, 53%; (b) Pd(Ph3P)4, Tl(OEt), THF/H2O (3:1), 28 °C, 15 min, 95%; (c) HF·pyridine, THF, −10 to 10 °C, 48 h, 87%.