Organic Chemistry

Total Synthesis and Prediction of Ulodione Natural Products Guided by DFT Calculations.

Authors

Abstract

A biomimetic synthetic strategy has resulted in a 2-step total synthesis of (±)-ulodione A and the prediction of two potential natural products, (±)-ulodiones C and D. This work was guided by computational investigations into the selectivity of a proposed biosynthetic Diels–Alder dimerization, which was then utilized in the chemical synthesis. This work highlights how biosynthetic considerations can both guide the design of efficient synthetic strategies and lead to the anticipation of new natural products.

Content

Thumbnail image of Ulodione manuscript.pdf

Supplementary material

Thumbnail image of Ulodione SI.pdf
Supporting Information
Overview of previous and current total synthesis, experimental procedures and analytical data for all compounds, and computational methods and analyses.
Thumbnail image of Ulodione geometries.zip
Molecular Geometries
Molecular geometries of all key stationary points.