Synthesis of vulpinic and pulvinic acids from tetronic acid

Bourdreux, Yann; Bodio, Ewen; Willis, Catherine; Billaud, Célia; Gall, Thierry Le; Mioskowski, Charles

doi:10.1016/j.tet.2008.06.058

Cited by 34 publications

(17 citation statements)

References 44 publications

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“…The starting methyl and benzyl tetronates 1a and 1b were either commercially available (i.e., 1a , R 1 = Me) or known (i.e., 1b , R 1 = Bn) 5b,5c. New lactones 1c and 1d were prepared in a similar manner to 1b in unoptimized yields of 50 and 37 %, respectively, by treating p ‐fluoro‐ and p ‐methoxybenzyl chlorides (1.1 equiv.)…”

Section: Resultsmentioning

confidence: 99%

A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization

et al. 2015

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The synthesis of a series of diverse methyl and benzyl γ‐ylidenetetronate derivatives was accomplished through the condensation of methyl and benzyl tetronates with (hetero)aryl aldehydes in a new two‐ or three‐step aldolisation/dehydration sequence. The bromination of methyl and benzyl γ‐ylidenetetronates occurred under mild conditions to provide the corresponding C‐3‐brominated γ‐unsaturated lactones. Di‐ and tribrominated γ‐lactones were prepared under slightly different conditions. Some brominated materials were employed in representative Stille, Suzuki–Miyaura, and Sonogashira cross‐coupling reactions to yield functionalized methyl and benzyl γ‐ylidenetetronate derivatives. Compounds that resulted from the Sonogashira cross‐coupling reactions were desilylated and converted into 1,2,3‐triazole derivatives through a copper(I)‐catalyzed 1,3‐dipolar cycloaddition reaction with benzyl azide.

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Section: Resultsmentioning

confidence: 99%

A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization

et al. 2015

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“…The chemistry involved features three sequential vinylogous aldol (or Mannich, vide infra) processes where heterocyclic dienoxy silane synthons TBSOF (157), TBSOT (164), and TBSOP (163) can be installed as wished during the stepwise elongation sequence. As an example, the synthesis of the C12-C25 bis-THF segment of asimicin (202), one of the most potent members of this family, is shown in Scheme 38.…”

Section: Diastereoselective and Unselective Processesmentioning

confidence: 99%

The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress

et al. 2011

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“…They are isolated from roots, tubers, knots, stalks, seeds and fruits [1,2,3] and have also been found in mushrooms and cyanobacteria [4,5]. They are reported to display a wide variety of biological activities such as anticancer [6,7], antioxidant [8,9], antifungal [10,11], antiviral [12,13], anti-inflammatory [14], antifeedant [15], anticonvulsant [16] and phytoestrogenic [17,18].…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of trans-β-Aryl-δ-hydroxy-γ-lactones and Enzymatic Kinetic Resolution of Their Racemic Mixtures

et al. 2016

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Two novel and convenient routes to obtain enantiomerically enriched trans-β-aryl-δ-hydroxy-γ-lactones 5a-d with potential antifeedant and anticancer activity were developed. In the first method starting from corresponding enantiomers of γ,δ-unsaturated esters 4a-d derived from enzymatically resolved allyl alcohols 1a-d, both enantiomers of hydroxylactones 5a-d were synthesized with high enantiomeric excesses (73%-97%). Configurations of the stereogenic centers of the synthesized compounds were assigned based on the mechanism of acidic lactonization of esters 4a-d in the presence of m-chloroperbenzoic acid (m-CPBA). An alternative method for the production of optically active trans-β-aryl-δ-hydroxy-γ-lactones 5a-d was lipase-catalyzed kinetic resolution of their racemic mixtures by transesterification with vinyl propionate as the acyl donor. The most efficient enzyme in the screening procedure was lipase B from Candida antarctica. Its application on a preparative scale after 6 h afforded unreacted (+)-(4S,5R,6S)-hydroxylactones 5a-d and (+)-(4R,5S,6R)-propionates 6a-d, most of them with high enantiomeric excesses (92%-98%). Resolution of lactone 5d with bulky 1,3-benzodioxol ring provided products with significantly lower optical purity (ee = 89% and 84% for hydroxylactone 5d and propionate 6d, respectively). The elaborated methods give access to both enantiomers of trans-β-aryl-δ-hydroxy-γ-lactones 5a-d with the defined absolute configurations of stereogenic centers, which is crucial requirement for the investigations of relationship: spatial structure-biological activity.

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Synthesis of vulpinic and pulvinic acids from tetronic acid

Cited by 34 publications

References 44 publications

A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization

A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization

The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress

Chemoenzymatic Synthesis of trans-β-Aryl-δ-hydroxy-γ-lactones and Enzymatic Kinetic Resolution of Their Racemic Mixtures

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Synthesis of vulpinic and pulvinic acids from tetronic acid

Cited by 34 publications

References 44 publications

A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective ­Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization

A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective ­Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization

The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress

Chemoenzymatic Synthesis of trans-β-Aryl-δ-hydroxy-γ-lactones and Enzymatic Kinetic Resolution of Their Racemic Mixtures

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A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization

A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization