Merging Strategy, Improvisation, and Conversation to Solve Problems in Target Synthesis

Frontier, Alison J.; Sinclair, Paul P.

doi:10.1021/acs.accounts.0c00804

Acc. Chem. Res.

2021

DOI: 10.1021/acs.accounts.0c00804

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Merging Strategy, Improvisation, and Conversation to Solve Problems in Target Synthesis

Alison J. Frontier

Paul P. Sinclair

Abstract: A novel transannular annulation strategy (iodo-aldol/oxa-Michael addition) is leveraged to construct the ABD ring system of phomactin A.

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2024

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Cited by 6 publications

References 95 publications

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Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Chen,

Zhang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryAs one of the most common structural motifs in natural products, cyclopentenones usually can be fabricated by Nazarov cyclization using divinyl ketones or functionalized tertiary divinyl carbinols (TDCs) as substrates. However, straightforward method for transforming unfunctionalized TDCs to their corresponding cyclopentenones is currently lacking. Herein, we wish to report the total syntheses of four structurally distinct terpenoids, namely laurane‐type marine sesquiterpenoids isolaurene, debromoaplysin and aplysin, and guaiane sesquiterpenoid guaiadienone A, all using a novel synthetic method, named oxidative Nazarov cyclization, as the key step. This work demonstrated our robust method is suitable for synthesizing various highly substituted cyclopentenones.

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Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Chen,

Zhang

et al. 2024

Chin. J. Chem.

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Recent advances in organic synthesis via synergistic nickel/copper catalysis

Liu

Huang

2023

Coordination Chemistry Reviews

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Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization

Xie,

Chen,

Zhang

et al. 2024

Cell Reports Physical Science

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Merging Strategy, Improvisation, and Conversation to Solve Problems in Target Synthesis

Abstract: A novel transannular annulation strategy (iodo-aldol/oxa-Michael addition) is leveraged to construct the ABD ring system of phomactin A.

Cited by 6 publications

References 95 publications

Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Recent advances in organic synthesis via synergistic nickel/copper catalysis

Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization

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