Synthesis of Bistratamide H Using a New Fluorous Protecting Group

Bistratamide H was expeditiously synthesized using a new fluorous protecting group, 2(tris(perfluorodecyl)silyl)ethoxycarbonyl ((F)Teoc) via a preparation of thiazole amino acid by a modified Hantzsch's method. The intermediates of the synthesis were easily isolated by fluorous liquid-liquid extraction. The fluorous protecting group was removed from the precursor of bistratamide H with TBAF and the recovered fluorous fragment, tris(perfluorodecyl)silylfluoride, was reacted with vinyl magnesium chloride to give an intermediate in the synthesis of (F)Teoc reagent.