481-64-1Relevant academic research and scientific papers
Catalytic Undirected Intermolecular C-H Functionalization of Arenes with 3-Diazofuran-2,4-dione: Synthesis of 3-Aryl Tetronic Acids, Vulpinic Acid, Pinastric Acid, and Methyl Isoxerocomate
Manchoju, Amarender,Pansare, Sunil V.
supporting information, p. 5952 - 5955 (2016/11/29)
A variety of 3-aryl tetronic acids have been synthesized by an undirected, intermolecular C-H functionalization of arenes with 3-diazofuran-2,4-dione. This methodology featured as a key step in the synthesis of a series of naturally occurring 3-aryl-5-arylidene tetronic acids (pulvinates) from commercially available tetronic acid. Salient features of the pulvinic acid synthesis include a one-step, stereoselective synthesis of the C5 arylidene group and a single step introduction of the C3 aryl substituent.
Synthesis and antioxidant properties of pulvinic acids analogues
Nadal, Brice,Thetiot-Laurent, Sophie A.-L.,Pin, Serge,Renault, Jean-Philippe,Cressier, Damien,Rima, Ghassoub,Le Roux, Antoine,Meunier, Stéphane,Wagner, Alain,Lion, Claude,Le Gall, Thierry
experimental part, p. 7931 - 7939 (2011/02/21)
The synthesis of three types of pulvinic acid analogues, using a diversity-oriented strategy starting from a single compound, dimethyl l-tartrate, is described. Lacey-Dieckmann condensation, alcohol dehydration and Suzuki-Miyaura cross-couplings were empl
Synthesis of vulpinic acids from dimethyl tartrate
Nadal, Brice,Thuéry, Pierre,Le Gall, Thierry
experimental part, p. 2430 - 2433 (2009/08/07)
A series of vulpinic acids differing by the aryl or heteroaryl groups placed in the ester α-position were prepared by Suzuki-Miyaura cross-coupling involving a common iodide and the corresponding aryl boronates. The preparation of the iodide precursor fro
3-Aryltetronic acids: Efficient preparation and use as precursors for vulpinic acids
Mallinger, Aurelie,Gall, Thierry Le,Mioskowski, Charles
supporting information; experimental part, p. 1124 - 1129 (2009/07/11)
3-Aryltetronic acids were prepared in one step by treatment of a mixture of methyl arylacetates and methyl hydroxyacetates with potassium tert-butoxide, via tandem transesterification/Dieckmann condensation. Several mushroom or lichen pigments, vulpinic acids, were synthesized from 3-(4-methoxyphe-nyl) tetronic acid in three steps involving the reaction of the corresponding dianion with an α-ketoester and the dehydration of the tertiary alcohols obtained into mixtures of (E)-and (Z)-alkenes, which were converted under UV irradiation at 254 nm to natural (E)-isomers. Syntheses of pinastric acid, 4,4′-dimethoxyvulpinic acid, and the first synthesis of recently isolated methyl 3′,5′-dichloro-4,4′-di-0-methylatromentate were hence achieved in an efficient manner.
Synthesis of vulpinic and pulvinic acids from tetronic acid
Bourdreux, Yann,Bodio, Ewen,Willis, Catherine,Billaud, Célia,Le Gall, Thierry,Mioskowski, Charles
, p. 8930 - 8937 (2008/12/22)
A common precursor, tetronic acid, was used in the synthesis of several vulpinic acids and pulvinic acids, which are pigments found in several lichens and mushrooms. The key features of this method are a two-step alkylidenation of benzyl tetronate and a Suzuki-Miyaura cross-coupling. The synthesis of several natural products, vulpinic acid, pinastric acid, xerocomic acid is described.
Flexible synthesis of vulpinic acids from tetronic acid
Willis, Catherine,Bodio, Ewen,Bourdreux, Yann,Billaud, Célia,Gall, Thierry Le,Mioskowski, Charles
, p. 6421 - 6424 (2008/02/12)
Several vulpinic acids were synthesized in a few steps from a single precursor, the tetronic acid. This commercial compound was converted in a few steps to an iodide. Suzuki-Miyaura cross-couplings involving this common intermediate and various arylboronates allowed to gain access to several vulpinic acids (or methyl pulvinates). Among them, two natural products, vulpinic acid and pinastric acid, were prepared.
Synthesis of natural pulvinic acids based on a '[3+2] cyclization-Suzuki cross-coupling' strategy
Ahmed, Zafar,Langer, Peter
, p. 2055 - 2063 (2007/10/03)
A number of pulvinic acid natural products were prepared based on Suzuki cross coupling reactions of α-hydroxy-γ-alkylidenebutenolides which are readily available by cyclization of 1,3-bis-silyl enol ethers with oxalyl chloride. The formal total synthesis
Synthesis of Grevillins, Novel Pyrandione Pigments of Fungi. Biogenetic Interrelationships between Grevillins, Pulvinic Acids, Terphenylquinones and Xylerythrins
Pattenden, Gerald,Pegg, Neil A.,Kenyon, Ronald W.
, p. 2363 - 2372 (2007/10/02)
A synthesis of the grevillin group of pyrandione pigments, e.g. 3, 23 and 24 present in fungi is described.The synthesis, which is based on a biogenetic model, uses bis-benzylacyloins 9 and their corresponding oxalate derivatives as key intermediates (Scheme 3).Treatment of the grevillins 25a-c with sodium ethoxide in ethanol effects their quantitative isomerisation into the corresponding terphenylquinone pigments 4a-c.Perkin-type condensations between the terphenylquinones 4 and arylacetic acids in the presence of sodium acetate-acetic anhydride then produces the xylerythrin pigments 29a-e, whereas rearrangements of 4 in the presence of dimethyl sulphoxide leads to pulvinic acid derivative, e.g. 31, 32 and 5.These synthetic studies interrelate the biosynthetic origins of the pigment types 3, 4, 5 and 8 together with the related pulvinones 6 and furanone 7 fungal pigments.
