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

Abstract

A biomimetic synthetic strategy has resulted in a two-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.

A bioinspired, one-step total synthesis of peshawaraquinone

“…those with multiple stereocenters) are rare. 2 A famous example is Chapman's total synthesis of carpanone via an unsymmetrical, oxidative dimerization of a simple phenol that constructs five stereocenters and two rings in a single step ( Fig. 1 ).…”