Stereoselective syntheses of naturally occurring 5,6-dihydropyran-2-ones

Marco, J. Alberto; Cardá, Miguel; Murga, Juan; Falomir, Eva

doi:10.1016/j.tet.2006.12.047

Cited by 122 publications

(50 citation statements)

References 284 publications

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“…They were used in the syntheses of macrolactin A [6] and natural (5'-oxoheptene-1'E,3'E-dienyl)-5,6-dihydro-2H-pyran-2-one. [7] In view of the aforementioned, along with the fact that enantioselective allylation could be an important step in syntheses of variousn atural compounds such as pteroenonead efensive metabolite (ichthyodeterrent) isolated from the Antarctic pteropod Clione antarctica, [8] tiacumicin antibiotics isolated from Dactylosporangium aurantiacum, [9] antillatoxin isolated from marine cyanobacterium Lyngbya majuscula [10] ( Figure 1) and other compounds [11] -we decided to screen various reaction conditions to assess the scope of allylation with respectt oc atalytic conditions. We chose (2E,4E)-2,4-dimethylhexadienal (2), prepared by using the previously published procedures from ethyl 2-bromopropionate, as am odel compound because its structuralf eature, represented by the substitutedd iene moiety,c an be found in the aforementioned natural compounds.…”

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confidence: 99%

Enantioselective Allylation of (2E,4E)‐2,4‐Dimethylhexadienal: Synthesis of (5R,6S)‐(+)‐Pteroenone

Koukal

Kotora

2015

Chemistry A European J

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Allylation, trans- and cis-crotylation of (2E,4E)-2,4-dimethylhexadienal, a representative α,β,γ,δ-unsaturated aldehyde, was carried out under different catalytic and stoichiometric conditions. The reactions catalyzed by organocatalysts TRIP-PA and N,N'-dioxides gave the best results with respect to yields, asymmetric induction, and catalyst load in comparison to other procedures. The developed methodology was applied in the enantioselective synthesis of (5R,6S)-(+)-pteroenone, a defensive metabolite (ichthyodeterrent) of the Antarctic pteropod Clione antarctica.

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confidence: 99%

Enantioselective Allylation of (2E,4E)‐2,4‐Dimethylhexadienal: Synthesis of (5R,6S)‐(+)‐Pteroenone

Koukal

Kotora

2015

Chemistry A European J

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“…They are part of many natural compounds, biologically active substances and drugs [1–4]. For instance, Zanamivir and Laninamivir which are recommended for the treatment and prophylaxis of influenza caused by influenza A and B viruses contain a 3,4-dihydro-2 H -pyran fragment [5].…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

Ievlev

Ершов

Belikov

et al. 2016

Beilstein J. Org. Chem.

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SummaryAn efficient diastereoselective approach for the synthesis of functionalized 3,4-dihydro-2H-pyran-4-carboxamides with variable frame was developed based on the reaction of available 4-oxoalkane-1,1,2,2-tetracarbonitriles (adducts of TCNE and ketones) with aldehydes in an acidic media. An unusual process of quasi hydrolysis of the cyano group was observed in the course of the described regio- and diastereoselective transformation.

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“…1 Synargentolide A 1a is such a lactone isolated from the acetone extract of the dried aerial parts of Syncolostemon argenteus of the Southern African genus Syncolostemon, a plant from the Ongoya forest in the Kwazulu-Natal midlands of South Africa. 2 Synargentolide 1a is structurally similar to anamarine 1c and the structure of 1b was proposed based on extensive NMR studies and has been recently revised to be 1a.…”

Section: Introductionmentioning

confidence: 99%