Neues vom Diels-Alder-Übergangszustand

A wide range of cyclohexadienones has been synthesised in order to study their reactivity and their regio- and stereoselectivity with the enantiopure diene 1 under high-pressure conditions. Computational investigations were used to point out some parameters which affect the reactivity in this high chiral discrimination process. In addition, the resulting [4+2] cycloadducts allowed the preparation of new polyfunctional cyclohexenone derivatives.

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New Cyclohexadienone Derivatives: Preparation and Chiral Discrimination in High-Pressure Diels-Alder Cycloadditions

Trân-Huu-Dâu

Wartchow

Winterfeldt

et al. 2001

Chem. Eur. J.

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Total Synthesis of the Ubiquitin‐Activating Enzyme Inhibitor (+)‐Panepophenanthrin

2003

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

Bestwick

Jones

et al. 2022

Angewandte Chemie

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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.

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Neues vom Diels-Alder-Übergangszustand

Cited by 8 publications

References 21 publications

New Cyclohexadienone Derivatives: Preparation and Chiral Discrimination in High-Pressure Diels-Alder Cycloadditions

New Cyclohexadienone Derivatives: Preparation and Chiral Discrimination in High-Pressure Diels-Alder Cycloadditions

Total Synthesis of the Ubiquitin‐Activating Enzyme Inhibitor (+)‐Panepophenanthrin

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

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