Total Synthesis of Tyrosine‐Derived Tetramic Acid Pigments from a Slime Mould

Riache, Nassima; Bailly, Christine; Deville, Alexandre; Dubost, Lionel; Nay, Bastien

doi:10.1002/ejoc.201000597

Cited by 15 publications

(16 citation statements)

References 17 publications

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“…β‐Ketoamide 8′ was obtained as a crude product not amenable to further purification. An attempted cyclization of 8′ under conditions described in the literature for simple unprotected N ‐acyl tyrosinates failed to give 31 , a diastereomer of F‐14329 and chaunolidine A, but afforded the retro‐aldol product 30 instead (Scheme ).…”

Section: Figurementioning

confidence: 99%

“…b-Ketoamide 8' was obtained as ac rude product not amenable to further purification. An attempted cyclization of 8' under conditions described in the literature for simple unprotected N-acyl tyrosinates [15] failed to give 31,adiastereomer of F-14329 and chaunolidine A, but afforded the retro-aldol product 30 instead (Scheme 5). To favor Dieckmann cyclization over retro-aldol fragmentation, we introduced an N-2,4-dimethoxybenzyl (DMB) group, previously shown by Schlessinger et al to render b-ketoamide anions more nucleophilic.…”

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confidence: 99%

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A Synthetic Route to β‐Hydroxytyrosine‐Derived Tetramic Acids: Total Synthesis of the Fungal Metabolite F‐14329

Bruckner

Haase

Schobert

2017

Chemistry A European J

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3-Acyltetramic acids derived from β-hydroxytyrosine are synthetically challenging. The first route to this structural motif, based upon a condensation between a Meldrum's acid conjugate bearing the acyl side chain, and a β-hydroxytyrosinate, N-protected by an ortho-nitrobenzyl group is presented. This group enables the Dieckmann cyclization of the resulting N-(β-ketoacyl)amino ester, after which it can be removed photolytically without compromising the delicate 3'-hydroxy group. This strategy was applied to the first total synthesis of the fungal metabolite F-14329 (1).

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Section: Figurementioning

confidence: 99%

mentioning

confidence: 99%

A Synthetic Route to β‐Hydroxytyrosine‐Derived Tetramic Acids: Total Synthesis of the Fungal Metabolite F‐14329

Bruckner

Haase

Schobert

2017

Chemistry A European J

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“…The phenol group of the tyrosine ethyl ester hydrochloride 9 was protected with TBDMSCl, resulting in 10 (81%). 34 A peptidic coupling between 10 and FA generated 11 (83%). The free alcohol of 11 was activated to a p -nitrophenyl carbonate 12 in the presence of pyridine (71%).…”

Section: Results and Discussionmentioning

confidence: 99%

Poly(carbonate–amide)s Derived from Bio-Based Resources: Poly(ferulic acid-co-tyrosine)

et al. 2014

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Ferulic acid (FA), a bio-based resource found in fruits and vegetables, was coupled with a hydroxyl-amino acid to generate a new class of monomers to afford poly(carbonate–amide)s with potential to degrade into natural products. l-Serine was first selected as the hydroxyl-amino partner for FA, from which the activated p-nitrophenyl carbonate monomer was synthesized. Unfortunately, polymerizations were unsuccessful, and the elimination product was systematically obtained. To avoid elimination, we revised our strategy and used l-tyrosine ethyl ester, which lacks an acidic proton on the α position of the ethyl ester. Four new monomers were synthesized and converted into the corresponding poly(carbonate–amide)s with specific regioselectivities. The polymers were fully characterized through thermal and spectroscopic analyses. Preliminary fluorescent studies revealed interesting photophysical properties for the monomers and their corresponding poly(carbonate–amide)s, beyond the fluorescence characteristics of l-tyrosine and FA, making these materials potentially viable for sensing and/or imaging applications, in addition to their attractiveness as engineering materials derived from renewable resources.

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“…To reach the biomimetic intermediate 6, retrosynthetic analysis revealed two Wittig-type olefinations (a) or (b). Indeed we and others have recently shown that activated acetyltetramic acids can be used in a variety of Horner-Wadsworth-Emmons 8 or Wittig 9 reactions to make long-chain-substituted tetramic acids from natural sources. Herein, we wish to describe our efforts to synthesize the polyunsaturated part of compound 6 from (R)-citronellal.…”

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confidence: 99%

“…Moreover, the one-pot diol cleavage-Wittig reaction sequences towards ester 18 and amide 19 from diol 13 have shown the feasibility of this strategy that we hope to apply to the synthesis of 6, through the a,b-unsaturated aldehyde 20, according to strategy (a). 8,9 In parallel, efforts are under way to synthesize an E,E,E biomimetic precursor analogous to 6, which may be useful for reactivity studies. Further details will be reported in due course.…”

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confidence: 99%

Synthetic Studies toward a Biomimetic Linear Precursor of Hirsutellones

Riache¹,

Ndoye²,

Li³

et al. 2011

Synlett

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In this paper we describe our efforts to synthesize the polyunsaturated part of a putative linear precursor of hirsutellones from (R)-citronellal, characterized by a terminal (E,Z,E)-triene alcohol. The geometry of this last moiety was installed by the alkyne reduction of an ene-yne-ene, under the Boland conditions [Zn(Ag,Cu), MeOH]. Under these conditions, we found that the presence of a diol functionality at the opposite of the linear chain, facing the alkyne, was necessary for the success of the reduction, an effect attributed to the chelation of an activated zinc species. Then one-pot diol cleavage-Wittig olefination allowed for further functionalization into a valuable a,b-unsaturated ester or Weinreb amide.

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Total Synthesis of Tyrosine‐Derived Tetramic Acid Pigments from a Slime Mould

Cited by 15 publications

References 17 publications

A Synthetic Route to β‐Hydroxytyrosine‐Derived Tetramic Acids: Total Synthesis of the Fungal Metabolite F‐14329

A Synthetic Route to β‐Hydroxytyrosine‐Derived Tetramic Acids: Total Synthesis of the Fungal Metabolite F‐14329

Poly(carbonate–amide)s Derived from Bio-Based Resources: Poly(ferulic acid-co-tyrosine)

Synthetic Studies toward a Biomimetic Linear Precursor of Hirsutellones

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