A Concise Route to α′‐Methoxy‐γ‐pyrones and Verticipyrone Based Upon the Desymmetrization of α,α′‐Dimethoxy‐γ‐pyrone

Paolis, Michaël De; Rosso, Helèna; Henrot, Matthias; Prandi, Cristina; d'Hérouville, Florent Le Boucher; Maddaluno, Jacques

doi:10.1002/chem.201001780

Cited by 20 publications

(13 citation statements)

References 33 publications

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“…Conversion of secondary hydroxyl to a methoxy group occurred smoothly by methylation using MeI and NaH. On the other hand, three‐step synthesis from dimethyl 3‐oxopentandioate gave allyl γ‐pyrone 12 , as reported previously 12 …”

Section: Resultssupporting

confidence: 71%

Structure–activity relationship study of the anti‐obesity natural product yoshinone A

et al. 2021

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Yoshinone A was derived from marine algae and shown to inhibit adipogenic differentiation. The natural compound is composed of a γ‐pyrone ring and a side chain and that contains two asymmetric carbons. Although their absolute configuration has been determined, there is no information available on the stereoisomers and their bioactivities. To address this question, we synthesized all four stereoisomers and measured their activities. We also prepared three more derivatives of yoshinone A and found that the stereo‐configuration inside the side chain, the γ‐pyrone ring, and bulkiness of the side chain all played important roles in its activity. Our findings should help to elucidate the mechanism of action of yoshinone A.

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Section: Resultssupporting

confidence: 71%

Structure–activity relationship study of the anti‐obesity natural product yoshinone A

et al. 2021

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“…As outlined in Scheme , our initial strategy involved nucleophilic addition to α,α′-dimethoxy-γ-pyrone 2 producing in fine vinylogous enolate 3b.Li a cornerstone for assembling the side chain of the target with the α′-methoxy-γ-pyrone motif . Thorough investigation revealed that intermediate 3b.Li is the result of a sequence of transformations including an unusual and selective 1,4-addition to 2 , lithium methoxide elimination of 3a , and deprotonation of 3b …”

Section: Resultsmentioning

confidence: 99%

“…Melting points were determined using a Kopfler hot stage apparatus and were uncorrected. Aldehyde E - 9 , γ-pyrone 12 , deoxyaureothin ( 13a ), and alcohol 5a are known compounds.…”

Section: Experimental Sectionmentioning

confidence: 99%

Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent

et al. 2016

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Amenable to late-stage preparation of analogues, a flexible and convergent total synthesis of (±)-aureothin is presented. The strategy was based on a desymmetrization of α,α'-dimethoxy-γ-pyrone by a process combining 1,4-addition and alkylation of vinylogous enolate to stereoselectively reach the backbone of the target. Palladium-catalyzed cyanation of an elaborated and isomerizable E,Z dienyl motif followed by Pinner cyclization enabled the construction of the tetrahydrofuran motif while a first approach based on a late-stage oxidation was unsuccessful.

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“…Although the effectiveness is lower than thiazolidinediones, different mode of action of the γ-pyrones may provide an opportunity of drug development from this new therapeutic scaffold for insulin resistance type 2 diabetes. The concise synthetic strategies [33,34,35,36] and interesting bioactivities of structurally related compounds have been reported [37,38]. On the base of these studies, further synthetic and biological studies of nocapyrone families could be inspiring.…”

Section: Discussionmentioning

confidence: 99%

Nocapyrones: α- and γ-Pyrones from a Marine-Derived Nocardiopsis sp.

et al. 2014

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One new α-pyrone (nocapyrone R (1)), and three known γ-pyrones (nocapyrones B, H and L (2–4)) were isolated from the culture extract of a Nocardiopsis strain collected from marine sediment. Structures of these compounds were determined on the basis of spectroscopic data including NMR and MS. γ-Pyrones 2–4 were found to induce adiponectin production in murine ST-13 preadipocyte cells but the α-pyrone 1 had no activity. The absolute configuration of the anteiso-methyl branching in 4 was determined by HPLC comparison of a degraded product of 4 with standard samples as a 2:3 enantiomeric mixture of (R)- and (S)-isomers.

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A Concise Route to α′‐Methoxy‐γ‐pyrones and Verticipyrone Based Upon the Desymmetrization of α,α′‐Dimethoxy‐γ‐pyrone

Cited by 20 publications

References 33 publications

Structure–activity relationship study of the anti‐obesity natural product yoshinone A

Structure–activity relationship study of the anti‐obesity natural product yoshinone A

Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent

Nocapyrones: α- and γ-Pyrones from a Marine-Derived Nocardiopsis sp.

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