First Enantioselective Synthesis and Absolute Stereochemistry Assignment of New Monoterpene Aldehyde‐Esters from <i>Bupleurum gibraltaricum</i>

Brémond, Paul; Audran, Gérard; Juspin, Thierry; Monti, H.

doi:10.1002/ejoc.200601080

Cited by 5 publications

(1 citation statement)

References 20 publications

(18 reference statements)

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“…Column chromatography allowed the isolation of 2 22 but unfortunately led to decomposition of the endoperoxide 3. Therefore, we reversed the dyade concept and allocated the nucleophilic part to the endoperoxide component, i.e.…”

Section: Resultsmentioning

confidence: 99%

Singlet oxygen addition to cyclo-1,3-hexadienes from natural sources and from organocatalytic enal dimerization

Griesbeck¹,

Kiff²,

Neudörfl³

et al. 2015

Arkivoc

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The photoxygenation reactions of the natural monoterpene aldehyde safranal (1) and its reduction product safranol (4) were studied and the endoperoxide 5 from safranol was isolated and characterized by single crystal X-ray analysis. A dyade synthesis using DCC coupling of safranol with artesunic acid delivered the reactive substrate 7 for 1,3-diene photooxygenation. Singlet oxygen reaction of the substrate 7 enabled the synthesis of the trioxane-endoperoxide dyade 8. The diastereoisomeric 1,3-cyclohexadienes 10 were obtained from the proline-catalyzed Diels-Alder dimerization of the Michael aldehyde 9. From the singlet oxygen addition with the diastereoisomeric substrates 10, only the kinetically preferred cis-endoperoxide 11 was formed.

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Section: Resultsmentioning

confidence: 99%

Singlet oxygen addition to cyclo-1,3-hexadienes from natural sources and from organocatalytic enal dimerization

Griesbeck¹,

Kiff²,

Neudörfl³

et al. 2015

Arkivoc

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Enantioselective Syntheses of the Proposed Structures of Kopeolin and Kopeolone

Miquet

Vanthuyne

Brémond

et al. 2013

Chemistry A European J

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The first total syntheses of the proposed structures of kopeolin (1) and kopeolone (3) have been achieved from a common enantiopure chiral building block obtained by a chemoenzymatic enantioconvergent methodology. The syntheses feature two key steps: a one-pot reduction/diastereoselective protonation followed by a highly diastereoselective addition of an organocerate. The synthetic structures were fully characterized and all stereocenters were confirmed. The results show that the two previously reported structures were not assigned correctly, and suggest an initial structural misassignment during the isolation of the natural products. Thus, two revised structures, 1' for kopeolin and 3' for kopeolone, are proposed.

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Hemisynthesis and odour properties of δ-hydroxy-γ-lactones and precursors derived from linalool

Mehl¹,

Bombarda²,

Vanthuyne³

et al. 2010

Food Chemistry

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First Enantioselective Synthesis and Absolute Stereochemistry Assignment of New Monoterpene Aldehyde‐Esters from Bupleurum gibraltaricum

Cited by 5 publications

References 20 publications

Singlet oxygen addition to cyclo-1,3-hexadienes from natural sources and from organocatalytic enal dimerization

Singlet oxygen addition to cyclo-1,3-hexadienes from natural sources and from organocatalytic enal dimerization

Enantioselective Syntheses of the Proposed Structures of Kopeolin and Kopeolone

Hemisynthesis and odour properties of δ-hydroxy-γ-lactones and precursors derived from linalool

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