A short synthesis of both enantiomers of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid

<div><div><div><div><p>A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows to achieve a high trans diastereoselectivity during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis require six product purifications and it provides (+)-brefeldin C in 18% overall yield.</p></div></div></div></div>

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Substance Overview for Dicarboxylic acid anhydrides

The MAK-Collection for Occupational Health and Safety ◽

10.1002/3527600418.mbe0dcsahyd ◽

2014 ◽

pp. 1-1

Keyword(s):

Dicarboxylic Acid ◽

Dicarboxylic Acid Anhydrides ◽

Acid Anhydrides

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A Short Synthesis of the Plant Alkaloid 4-Methyl-2,6-naphthyridine

Letters in Organic Chemistry ◽

10.2174/1570178616666181116110647 ◽

2019 ◽

Vol 16 (12) ◽

pp. 931-934 ◽

Cited By ~ 2

Author(s):

Alexandra Kamlah ◽

Franz Bracher

Keyword(s):

Pyridine Ring ◽

Cross Coupling ◽

Antirrhinum Majus ◽

New Synthesis ◽

Short Synthesis ◽

Regioselective Oxidation ◽

Key Steps

: A new synthesis of the 2,6-naphthyridine alkaloid 4-methyl-2,6-naphthyridine from Antirrhinum majus has been developed. Key steps are a regioselective oxidation of 3-bromo-4,5- dimethylpyridine to the corresponding 4-formyl derivative, and the annulation of the second pyridine ring by Suzuki-Miyaura cross-coupling using (E)-2-ethoxyvinylboronic acid pinacol ester as a masked acetaldehyde equivalent. This protocol gives the alkaloid in four steps starting from commercially available 3,4-dimethylpyridine in 15% overall yield. This annulation protocol should be useful for the synthesis of other condensed pyridines as well.

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Efficient One-pot HATU Mediated Coupling of Dicarboxylic Acid and Amines for the Synthesis of Diamide at Ambient Temperature

Letters in Organic Chemistry ◽

10.2174/1570178614666170710095437 ◽

2017 ◽

Vol 14 (10) ◽

Cited By ~ 1

Author(s):

Vimal Bhatt ◽

S. D. Samant ◽

Suhas Pednekar

Keyword(s):

Ambient Temperature ◽

Dicarboxylic Acid ◽

One Pot

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SYNTHESIS, CHARACTERIZATION, DNA BINDING, AND ANTICANCER ABILITY OF A Co(II) COMPLEX CONSTRUCTED BY 2-PROPYL-1H-IMIDAZOLE-4,5-DICARBOXYLIC ACID

Journal of Structural Chemistry ◽

10.1134/s0022476620120112 ◽

2020 ◽

Vol 61 (12) ◽

pp. 1938-1944

Author(s):

S. Wu ◽

S. Wang ◽

M. Zhu ◽

E. Gao

Keyword(s):

Dna Binding ◽

Dicarboxylic Acid

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IR and 13C, 17O, and 119Sn NMR spectra of some bis(1-butyl)tin(IV) carboxylates of dicarboxylic acids

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19911908 ◽

1991 ◽

Vol 56 (9) ◽

pp. 1908-1915 ◽

Cited By ~ 18

Author(s):

Jaroslav Holeček ◽

Antonín Lyčka ◽

Milan Nádvorník ◽

Karel Handlíř

Keyword(s):

Infrared Spectroscopy ◽

Nmr Spectroscopy ◽

Dicarboxylic Acid ◽

Nmr Spectra ◽

Dicarboxylic Acids ◽

119Sn Nmr ◽

Carboxylic Groups ◽

Cyclic Oligomers ◽

The Media ◽

Oxygen Atoms

Infrared spectroscopy and multinuclear (13C, 17O, and 119Sn NMR spectroscopy have been used to study the structure of bis(1-butyl)tin(IV) carboxylates of dicarboxylic acids (1-C4H9)2. Sn(X(COO)2), where X = (CH2)n (n = 0-8), CH=CH (cis and trans) and C6H4 (ortho and para).The crystalline compounds are formed by linear or cyclic oligomers or polymers whose basic building units represent a grouping composed of the central tin atom substituted by two 1-butyl groups and coordinated with both oxygen atoms of two anisobidentate carboxylic groups derived from different molecules of a dicarboxylic acid. The environment of the tin atom has a shape of a trapezoidal bipyramid. When dissolvet in non-coordinating solvents, the compounds retain the oligomeric character with unchanged structure of environment of the central tin atom. In the media of coordinating solvents the bis(1-butyl)tin(IV) carboxylates of dicarboxylic acids form complexes whose central hexacoordinated tin atom binds two molecules of the solvent trough their donor atoms. Carboxylic groups form monodenate linkages in these complexes.

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