Synthesis of the spiroimine fragment of portimines A and B

Ding, Xiao-Bo; Wung, Alexander; Furkert, Daniel P.; Brimble, Margaret A.

doi:10.1039/d3ob00998j

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00998j

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Synthesis of the spiroimine fragment of portimines A and B

Xiao-Bo Ding,

Alexander Wung,

Daniel P. Furkert

et al.

Abstract: Portimines A and B are spirocyclic imine natural products, which display remarkable anticancer, anti-HIV, and antifouling activities. Herein, we report a facile synthesis of the spirocyclic core of portimines A...

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2024

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Cited by 2 publications

References 58 publications

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Synthesis of the Spirocyclic Imine Fragment of Portimines Using a γ-Hydroxymethyl-α,β-butenolide Dienophile in a Diastereoselective Diels–Alder Reaction

Kuang,

Ding,

et al. 2024

ACS Omega

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The synthesis of the spirocyclic imine fragment of the portimine family of marine toxins has been achieved. A densely functionalized key lactone-ester intermediate was assembled via a highly diastereoselective Diels−Alder cycloaddition, involving a novel γ-hydroxymethyl-α,β-butenolide dienophile. A Stille coupling was employed to install the vinyl group. Selective elaboration of the two carbonyl groups successfully afforded the spirocyclic imine fragment.

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Synthesis of the Spirocyclic Imine Fragment of Portimines Using a γ-Hydroxymethyl-α,β-butenolide Dienophile in a Diastereoselective Diels–Alder Reaction

Kuang,

Ding,

et al. 2024

ACS Omega

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Synthesis and α-Functionalisation of Cyclic Imines

Brimble,

Kuang,

Ding

et al. 2024

Synlett

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-Functionalisation of cyclic imines has been explored. The cyclic imine substrates were synthesised from their respective halonitrile precursors using a nucleophilic addition/cyclisation sequence. Selective monohalogenation of the cyclic imines yielded alpha-haloimines, which served as a platform to obtain various alpha-hydroxyimine derivatives. In addition, an unusual tautomerisation and oxidation sequence was observed in the attempted preparation of alpha-hydroxyimines.

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Synthesis of the spiroimine fragment of portimines A and B

Abstract: Portimines A and B are spirocyclic imine natural products, which display remarkable anticancer, anti-HIV, and antifouling activities. Herein, we report a facile synthesis of the spirocyclic core of portimines A...

Cited by 2 publications

References 58 publications

Synthesis of the Spirocyclic Imine Fragment of Portimines Using a γ-Hydroxymethyl-α,β-butenolide Dienophile in a Diastereoselective Diels–Alder Reaction

Synthesis of the Spirocyclic Imine Fragment of Portimines Using a γ-Hydroxymethyl-α,β-butenolide Dienophile in a Diastereoselective Diels–Alder Reaction

Synthesis and α-Functionalisation of Cyclic Imines

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