4-O-Methyllividic acid
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| Category | Others |
| Catalog number | BBF-04862 |
| CAS |
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Description
4-O-Methyllividic acid is a new lichen depsidone.
Reference Reading
1. Synthesis and Application of Constrained Amidoboronic Acids Using Amphoteric Boron-Containing Building Blocks
Harjeet S Soor, Diego B Diaz, Ka Yi Tsui, Karina Calvopiña, Marcin Bielinski, Dean J Tantillo, Christopher J Schofield, Andrei K Yudin J Org Chem. 2022 Jan 7;87(1):94-102. doi: 10.1021/acs.joc.1c02015. Epub 2021 Dec 13.
Amidoboronic acid-containing peptidomimetics are an important class of scaffolds in chemistry and drug discovery. Despite increasing interest in boron-based enzyme inhibitors, constrained amidoboronic acids have received little attention due to the limited options available for their synthesis. We describe a new methodology to prepare both α- and β-amidoboronic acids that impose restrictions on backbone angles. Lewis acid-promoted Boyer-Schmidt-Aube lactam ring expansions using an azidoalkylboronate enabled generation of constrained α-amidoboronic acid derivatives, whereas assembly of the homologous β-amidoboronic acids was achieved through a novel boronic acid-mediated lactamization process stemming from an α-boryl aldehyde. The results of quantum chemical calculations suggest carboxylate-boron coordination to be rate-limiting for small ring sizes, whereas the tetrahedral intermediate formation is rate limiting in the case of larger rings. As part of this study, an application of β-amidoboronic acid derivatives as novel VIM-2 metallo-β-lactamase inhibitors has been demonstrated.
2. Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis: Synthesis of Phenanthrenes via Phosphomolybdic Acid as a Catalyst
Yi Chen, Di Liu, Rui Wang, Li Xu, Jingyao Tan, Mao Shu, Lingfeng Tian, Yuan Jin, Xiaoke Zhang, Zhihua Lin J Org Chem. 2022 Jan 7;87(1):351-362. doi: 10.1021/acs.joc.1c02385. Epub 2021 Dec 20.
Compared with the impressive achievements of catalytic carbonyl-olefin metathesis (CCOM) mediated by Lewis acid catalysts, exploration of the CCOM through Brønsted acid-catalyzed approaches remains quite challenging. Herein, we disclose a synthetic protocol for the construction of a valuable polycycle scaffold through the CCOM with the inexpensive, nontoxic phosphomolybdic acid as a catalyst. The current annulations could realize carbonyl-olefin, carbonyl-alcohol, and acetal-alcohol in situ CCOM reactions and feature mild reaction conditions, simple manipulation, and scalability, making this strategy a promising alternative to the Lewis acid-catalyzed COM reaction.
3. Hydrogen Peroxide-Responsive Triggers Based on Borinic Acids: Molecular Insights into the Control of Oxidative Rearrangement
Blaise Gatin-Fraudet, Mathilde Pucher, Thomas Le Saux, Gilles Doisneau, Yann Bourdreux, Ludovic Jullien, Boris Vauzeilles, Dominique Guianvarc'h, Dominique Urban Chemistry. 2022 Oct 21;28(59):e202201543. doi: 10.1002/chem.202201543. Epub 2022 Aug 26.
Arylborinic acids represent new, efficient, and underexplored hydrogen peroxide-responsive triggers. In contrast to boronic acids, two concomitant oxidative rearrangements are involved in the complete oxidation of these species, which might represent a major limitation for an efficient effector (drug or fluorophore) release. Herein, a comprehensive study of H2 O2 -mediated unsymmetrical arylborinic acid oxidation to investigate the factors that could selectively guide their oxidative rearrangement is described. The o-CF3 substituent was found to be an excellent directing group allowing a complete regioselectivity on borinic acid models. This result was successfully applied to synthesizing new borinic acid-based fluorogenic probes, which exclusively release the fluorescent moiety upon H2 O2 treatment. These compounds maintained their superior kinetic properties compared to boronic acids, thus further enhancing the potential of arylborinic acids as valuable new H2 O2 -sensitive triggers.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
