Biomimetic synthesis of fluvirosaone A

Abstract

Over the past century, biomimetic synthesis has significantly enhanced our understanding of the biosynthetic pathways involved in the formation of natural products. In this article, we present a two-step biomimetic synthesis of fluvirosaone A from 2,3-dehydroallosecurinine, featuring a Nazarov-type cyclization as the key step. Based on our synthetic results and computational analysis, we propose an alternative biosynthetic route for fluvirosaone A, identifying pyruvaldehyde as the likely source of the extraneous three carbons incorporated into the securinega skeleton.