Synthesis of Nitrogen-containing Natural Products Using Allyl Cyanate-to-isocyanate Rearrangement

Abstract

Over the last few years, we have embarked on the development of the synthesis of allyl cyanate and its rearrangement. This reaction offers an efficient transformation of the allyl alcohols into the allyl amines with high stereospecific manner even when the allyl alcohols are highly substituted at the γ-positions. Applications of this rearrangement in the context of the natural product synthesis have realized a new approach to the synthesis of amino-sugars, a new protocol for stereocontrolled allyl amine synthesis, and the first total synthesis of the peptidyl nucleoside antibiotic, blasticidin S.