An Enantiospecific Synthesis of Jiadifenolide

Abstract

Our strategy towards the synthesis of the neurotrophic natural product jiadifenolide is discussed. Jiadifenolide is a structurally complex seco-prezizaane natural product and our goals were to simplify the total synthesis of this compound using late stage C-H functionalization. It is our belief that the explorations into these late stage C-H functionalizations have taught us about the necessity for new technologies in this area while also demonstrating an effective strategy for the synthesis of these compounds. During the course of this synthesis many lessons were learned and some of the highlights included the use of the under utilized van Leusen reaction, the first use of Sanford's methyl acetoxylation in a synthesis, and the use of Danishefsky's iodoso Pummerer-like rearrangement.