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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.

SUBMITTER: Bestwick JS 

PROVIDER: S-EPMC9401604 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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

Bestwick Jacob S JS   Jones David J DJ   Jones Helen E HE   Kalomenopoulos Panagiotis G PG   Szabla Rafal R   Lawrence Andrew L AL  

Angewandte Chemie (International ed. in English) 20220628 32


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 nat  ...[more]

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