Amphidinolides F and C2: An Odyssey in Total Synthesis

Ferrié, Laurent; Ciss, Ismaïla; Fenneteau, Johan; Vallerotto, Sara; Seck, Matar; Figadère, Bruno

doi:10.1021/acs.joc.1c02458

Cited by 10 publications

(26 citation statements)

References 107 publications

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“… 4 Selective cleavage of the primary TES ether to produce alcohol 44 and subsequent oxidation with the Dess–Martin periodinane afforded aldehyde 45 . It should be noted that this aldehyde is the direct TES ether analogue of intermediates prepared by the groups of Armstrong and Ferrié during their studies on the synthesis of amphidinolide F. 5 , 18 Direct formation of dithiane 40 by the Lewis acid mediated reaction of aldehyde 45 with 1,3-propanedithiol was attempted to shorten the sequence in Scheme 6 , but decomposition of aldehyde 45 was observed.…”

Section: Resultsmentioning

confidence: 99%

“… 15 These meticulous and extensive synthetic studies have culminated in the recent total syntheses of amphidinolides F and C by the groups of Fürstner and Carter 16 , 17 and the total syntheses of amphidinolides F and C2 by the group of Ferrié. 18 …”

Section: Introductionmentioning

confidence: 99%

“…Over the past two decades, substantial portions of all four compounds have been synthesized by the groups of Kobayashi (C1–C10; C17–C29), Armstrong (C18–C29), Carter (C7–C20), Dai (C18–C26), Ferrié (C1–C9), Forsyth (C1–C9; C11–C25; C1–C14; C15–C25), Mohapatra (C1–C9; C19–C34), Morken (C1–C15), Pagenkopf (C1–C9; C18–C34), Roush (C1–C9; C11–C29), Spilling (C1–C9; C18–C29; C18–C34), and Williams (C10–C25) . These meticulous and extensive synthetic studies have culminated in the recent total syntheses of amphidinolides F and C by the groups of Fürstner and Carter , and the total syntheses of amphidinolides F and C2 by the group of Ferrié …”

Section: Introductionmentioning

confidence: 99%

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Convergent Synthesis of the C1–C29 Framework of Amphidinolide F

2022

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The complete carbon framework of the macrocyclic marine natural product amphidinolide F has been prepared by a convergent synthetic route in which three fragments of similar size and complexity have been coupled. Key features of the syntheses of the fragments include the stereoselective construction of the tetrahydrofuran in the C1–C9 fragment by oxonium ylide (free or metal-bound) formation and rearrangement triggered by the direct generation of a rhodium carbenoid from 1-sulfonyl-1,2,3-triazole, the highly diastereoselective aldol reaction between a boron enolate and an aldehyde with 1,4-control to prepare the C10–C17 fragment, and the formation of the tetrahydrofuran in the C18–C29 fragment by intramolecular nucleophilic ring opening of an epoxide with a hydroxyl group under acidic conditions.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Convergent Synthesis of the C1–C29 Framework of Amphidinolide F

2022

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“…Dess–Martin oxidation of the alcohol 15 to give the aldehyde 16 and subsequent Pinnick oxidation delivered the carboxylic acid 17 (fragment i in Figure ). , …”

mentioning

confidence: 99%

“…Amphidinolide F and related amphidinolides are alluring synthetic targets because of their structural complexity and reported biological activities. Myriad synthetic strategies for the stereoselective construction of key fragments of amphidinolide F have been explored in recent years, and many of them are also directly applicable to the synthesis of members of the amphidinolide C series because of the structural similarity of the compounds. − This work has resulted in the total syntheses of amphidinolide F by the groups of Fürstner, Carter, and Ferrié; syntheses of amphidinolides C and C2 have also been completed by these research groups.…”

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confidence: 99%

Synthetic Studies on Amphidinolide F: Exploration of Macrocycle Construction by Intramolecular Stille Coupling

Decultot

Clark

2022

Org. Lett.

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Exploration of an ambitious new strategy for the total synthesis of the cytotoxic marine natural product amphidinolide F is described, which features fabrication of the core structure from four readily accessible fragments and macrocycle construction through C9–C10 bond formation by intramolecular Stille coupling between an alkenyl iodide and alkenyl stannane. Efficient stereoselective synthesis of each of the four building-blocks and subsequent coupling of them to produce the requisite cyclization precursor has been accomplished, but suitable conditions for high-yielding palladium-mediated closure of the macrocycle to produce the fully protected amphidinolide F ring system have yet to be identified.

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Macrocyclization Strategies Towards the Synthesis of Amphidinolide Natural Products

2023

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dinoflagellates amphidinolide group of natural products have drawn the attention of the synthetic community owing to their natural scarcity, variation in ring size (12-to 27-membered), and architectural complexity. The manifold strategies for creating the unique macrocyclic framework of amphidinolides, overcoming the entropy barrier of cyclisation, in good yields and selectivity, are highly encouraging as this platform provides an opportunity to develop compounds for structure-activity relationship studies. This review emphasizes various methods of intramolecular CÀ C and CÀ O bondforming reactions for constructing the macrocyclic structure of different naturally occurring molecules of amphidinolide family.

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Amphidinolides F and C2: An Odyssey in Total Synthesis

Cited by 10 publications

References 107 publications

Convergent Synthesis of the C1–C29 Framework of Amphidinolide F

Convergent Synthesis of the C1–C29 Framework of Amphidinolide F

Synthetic Studies on Amphidinolide F: Exploration of Macrocycle Construction by Intramolecular Stille Coupling

Macrocyclization Strategies Towards the Synthesis of Amphidinolide Natural Products

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