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. 2019 Jul 23;15:1722–1757. doi: 10.3762/bjoc.15.168

Scheme 11.

Scheme 11

Synthesis of xestoaminol C ((2S,3R)-35), 3-epi-xestoaminol C ((2S,3S)-35) and N-Boc-spisulosine ((2S,3R)-38). Reagents and conditions: a) C11H23Br, Mg, THF, 0 °C, 1 h; b) NaBH4, ZnCl2, MeOH, 78 °C, 2 h; c) ʟ-Selectride®, THF, −78 °C, 1 h; d) H2, Pd(OH)2, Boc2O, MeOH, rt 6 h; e) HCl, MeOH, reflux, 3 h.