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

Jacob Bestwick; David Jones; Helen Jones; Panagiotis Kalomenopoulos; Rafal Szabla; Andrew Lawrence

doi:10.26434/chemrxiv-2022-2x0b1

Organic Chemistry

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

Working Paper

Jacob Bestwick University of Edinburgh ,
David Jones University of Edinburgh ,
Helen Jones University of Edinburgh ,
Panagiotis Kalomenopoulos University of Edinburgh ,
Rafal Szabla Wrocław University of Science and Technology ,
Andrew Lawrence University of Edinburgh

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

Supporting Information

Overview of previous and current total synthesis, experimental procedures and analytical data for all compounds, and computational methods and analyses.