Synthetic Studies of Nitrogen-containing Terpenes Originated from Marine Organism Using Sigmatropic Rearrangement and Ritter Reaction

Abstract

Synthetic studies of nitrogen-containing terpenes isolated from marine organism are described. Agelasidine A was synthesized by using hetero-Claisen rearrangement of allyl xanthate. Biomimetic synthesis of agelasidine A employing sigmatropic rearrangement of allyl sulfinate realized three-step synthesis starting from farnesol. Biomimetic synthesis of aminobisabolene and theonellin using the Ritter reaction was achieved. Allyl cyanate-to-isocyanate rearrangement was established as a new synthetic method for the construction of allyl amine moiety at sterically congested positions. Application of this new method completed the synthesis of geranyllinaloisocyanide.