An Efficient Synthesis of Chiral Non‐Racemic Hydroxyalkanoic Acids by Olefin Cross‐Metathesis Reactions

Asaro, Fioretta; Drioli, Sara; Forzato, Cristina; Nitti, Patrizia

doi:10.1002/slct.201802989

Cited by 5 publications

(3 citation statements)

References 57 publications

(29 reference statements)

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“…Concomitant with the work of Pflimlin et al [13], Asaro et al [33] carried out similar olefin cross-coupling reaction with (R)-or (S)-secondary allylic alcohols. The latter were prepared by kinetic resolution of the corresponding racemic alcohol in lipase-catalyzed transesterification [34].…”

Section: Optically Active Fahfasmentioning

confidence: 99%

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Understanding FAHFAs: From structure to metabolic regulation

Brejchová

Balas

Paluchová

et al. 2020

Progress in Lipid Research

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HAL is a multi-disciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

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Section: Optically Active Fahfasmentioning

confidence: 99%

“…The enzymatic reactions proceeded with high enantioselectivity (97-100%), although a limitation may be the difficulty in identifying a suitable lipase and optimized conditions. The Asaro approach provided both pure (R)-and (S)-8-HFA enantiomers with good yields [33].…”

Section: Optically Active Fahfasmentioning

confidence: 99%

Understanding FAHFAs: From structure to metabolic regulation

Brejchová

Balas

Paluchová

et al. 2020

Progress in Lipid Research

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“…The configuration of the chiral center was shown [18] to be of great importance for the rate of their biosynthesis and ester linkage hydrolysis (see section V). Thus, for the last three years, organic chemists focused their efforts on stereocontrolled multistep strategies, providing several enantio-pure or enantio-enriched FAHFAs, using (R)-and (S)-chiral pools [epichlorohydrin epimers [18,19]; (S)-glycidol [20]; (R)-glyceraldehyde [21]; D-glucose derivatives [22e24] or asymmetric enantioselective reactions (asymmetric Jorgensen epoxidation [25,26]; asymmetric allylations [27,28]; lipase-catalyzed transesterification [29]; asymmetric hydrogenation [30], respectively. Both (R)-and (S)-enantiomers were detected in vivo [18,31].…”

Section: Synthesis Of Fahfas To Help In Understanding the Endogenous Fahfa Systemmentioning

confidence: 99%

Potential physio-pathological effects of branched fatty acid esters of hydroxy fatty acids

Benlebna¹,

Balas

Gaillet³

et al. 2021

Biochimie

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Branched Fatty Acid Esters of Hydroxy Fatty Acids (FAHFAs) are a new endogenous lipid class with recently uncovered interesting biological effects and which have been detected in food of plant and animal origins. Some FAHFAs can improve glucose tolerance and insulin sensitivity, stimulate insulin secretion, and exert anti-inflammatory effects. Other beneficial health effects have also been suggested, in particular against some cancers. FAHFAs could therefore be a potential therapeutic target for the treatment of numerous metabolic disorders such as type II diabetes, hepatic steatosis, cardiovascular diseases and various cancers. Their recent discovery has generated a great interest in the field of human health. This short review aims at bringing together the information available to date in the literature concerning their chemical synthesis, biosynthesis and degradation pathways as well as their potential physio-pathological beneficial effects. Contents

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Asymmetric Synthesis of Saturated Hydroxy Fatty Acids and Fatty Acid Esters of Hydroxy Fatty Acids

et al. 2019

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The recent discovery of a novel class of endogenous lipids, named Fatty Acid esters of Hydroxy Fatty Acids (FAHFAs), that present antidiabetic and anti‐inflammatory activities, has attracted the interest on hydroxy fatty acids (HFAs) and their derivatives. We present herein the development of a convenient and general methodology for the asymmetric synthesis of HFAs and FAHFAs. The enantioselective organocatalytic synthesis of asymmetric terminal epoxides starting from monoprotected α,ω‐diols and their subsequent ring opening by a Grignard reagent are the key‐steps for our methodology, allowing the introduction of the hydroxy group at different positions of the long chain by proper selection of the starting diol and the Grignard reagent. MacMillan's third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, an approach for the synthesis of deuterated HFAs and FAHFAs was developed, leading to deuterated derivatives, which can be useful in biological studies and in mass spectrometry studies as internal standards.

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An Efficient Synthesis of Chiral Non‐Racemic Hydroxyalkanoic Acids by Olefin Cross‐Metathesis Reactions

Cited by 5 publications

References 57 publications

Understanding FAHFAs: From structure to metabolic regulation

Understanding FAHFAs: From structure to metabolic regulation

Potential physio-pathological effects of branched fatty acid esters of hydroxy fatty acids

Asymmetric Synthesis of Saturated Hydroxy Fatty Acids and Fatty Acid Esters of Hydroxy Fatty Acids

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