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

Jacob S. Bestwick; David J. Jones; Helen E. Jones; Panagiotis G. Kalomenopoulos; Rafal Szabla; Andrew Leslie Lawrence

doi:10.1002/anie.202207004

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

Jacob S. Bestwick, David J. Jones, Helen E. Jones, Panagiotis G. Kalomenopoulos, Rafal Szabla, Andrew Leslie Lawrence

Research output: Contribution to journal › Article › peer-review

Abstract / Description of output

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.

Original language	English
Journal	Angewandte Chemie International Edition
Early online date	7 Jun 2022
DOIs	https://doi.org/10.1002/anie.202207004
Publication status	E-pub ahead of print - 7 Jun 2022

Access to Document

10.1002/anie.202207004

20220701_Lawrence_Bestwick_Angew-VoRFinal published version, 1.97 MBLicence: Creative Commons: Attribution-NonCommercial-NoDerivatives (CC BY-NC-ND)

https://onlinelibrary.wiley.com/doi/10.1002/anie.202207004

Stereoretentive-Enantioconvergent Catalysis: A New Concept in Asymmetric Synthesis
Lawrence, A.
EU government bodies
1/11/17 → 30/04/23
Project: Research

Cite this

@article{6ad228cd6240463691b041bdea50977d,

title = "Total Synthesis and Prediction of Ulodione Natural Products Guided by DFT Calculations",

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.",

author = "Bestwick, {Jacob S.} and Jones, {David J.} and Jones, {Helen E.} and Kalomenopoulos, {Panagiotis G.} and Rafal Szabla and Lawrence, {Andrew Leslie}",

note = "Funding Information: This work was supported by funding from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (Grant Agreement No. 759552). H.E.J. thanks the University of Edinburgh for the provision of a studentship. Lauren Bertram and Baekman Kim (University of Edinburgh) are acknowledged for conducting preliminary DFT calculations. DFT calculations were performed with resources granted by the Wroc{\l}aw Centre for Networking and Supercomputing (WCSS). Publisher Copyright: {\textcopyright} 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

year = "2022",

month = jun,

day = "7",

doi = "10.1002/anie.202207004",

language = "English",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "Wiley-VCH",

}

TY - JOUR

T1 - Total Synthesis and Prediction of Ulodione Natural Products Guided by DFT Calculations

AU - Bestwick, Jacob S.

AU - Jones, David J.

AU - Jones, Helen E.

AU - Kalomenopoulos, Panagiotis G.

AU - Szabla, Rafal

AU - Lawrence, Andrew Leslie

N1 - Funding Information: This work was supported by funding from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (Grant Agreement No. 759552). H.E.J. thanks the University of Edinburgh for the provision of a studentship. Lauren Bertram and Baekman Kim (University of Edinburgh) are acknowledged for conducting preliminary DFT calculations. DFT calculations were performed with resources granted by the Wrocław Centre for Networking and Supercomputing (WCSS). Publisher Copyright: © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

PY - 2022/6/7

Y1 - 2022/6/7

N2 - 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.

AB - 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.

U2 - 10.1002/anie.202207004

DO - 10.1002/anie.202207004

M3 - Article

SN - 1433-7851

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

ER -

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

Abstract / Description of output

Access to Document

Fingerprint

Projects

Stereoretentive-Enantioconvergent Catalysis: A New Concept in Asymmetric Synthesis

Cite this