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Literature DB >> 32573211

Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation.

Steven W M Crossley¹, Guanghu Tong¹, Michael J Lambrecht¹, Hannah E Burdge¹, Ryan A Shenvi¹.

Abstract

We report a concise, stereocontrolled synthesis of the neurotoxic sesquiterpenoid (-)-picrotoxinin (1, PXN). The brevity of the route is due to regio- and stereoselective formation of the [4.3.0] bicyclic core by incorporation of a symmetrizing geminal dimethyl group at C5. Dimethylation then enables selective C-O bond formation in multiple intermediates. A series of strong bond (C-C and C-H) cleavages convert the C5 gem-dimethyl group to the C15 lactone of PXN.

Entities: Chemical Disease Gene Species

Mesh：

Substances：
Picrotoxin
picrotoxinin

Year: 2020 PMID： 32573211 PMCID： PMC8011636 DOI： 10.1021/jacs.0c05042

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

19 in total

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Authors: Thomas Böttcher
Journal: J Chem Inf Model Date: 2016-02-22 Impact factor: 4.956

2. An eight-step gram-scale synthesis of (-)-jiadifenolide.

Authors: Hai-Hua Lu; Michael D Martinez; Ryan A Shenvi
Journal: Nat Chem Date: 2015-06-15 Impact factor: 24.427

3. Pharmacological characterization of the neurotrophic sesquiterpene jiadifenolide reveals a non-convulsant signature and potential for progression in neurodegenerative disease studies.

Authors: Jeffrey M Witkin; Ryan A Shenvi; Xia Li; Scott D Gleason; Julie Weiss; Denise Morrow; John T Catow; Mark Wakulchik; Masaki Ohtawa; Hai-Hua Lu; Michael D Martinez; Jeffrey M Schkeryantz; Timothy S Carpenter; Felice C Lightstone; Rok Cerne
Journal: Biochem Pharmacol Date: 2018-06-22 Impact factor: 5.858

Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation.

1. An Additive Definition of Molecular Complexity.

2. An eight-step gram-scale synthesis of (-)-jiadifenolide.

3. Pharmacological characterization of the neurotrophic sesquiterpene jiadifenolide reveals a non-convulsant signature and potential for progression in neurodegenerative disease studies.

4. Structural aspects of picrotoxinin action.

5. Pharmacotherapy for cognitive impairment in a mouse model of Down syndrome.

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Review 7. Modern synthetic efforts toward biologically active terpenes.

8. Radical Retrosynthesis.

9. Synthesis of (+)-zerumin B using a regioselective singlet oxygen furan oxidation.

10. Dynamic Strategic Bond Analysis Yields a Ten-Step Synthesis of 20-nor-Salvinorin A, a Potent κ-OR Agonist.

Review 1. GABA_A receptors: structure, function, pharmacology, and related disorders.

Review 2. Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis.

3. Synthetic, Mechanistic, and Biological Interrogation of Ginkgo biloba Chemical Space En Route to (-)-Bilobalide.

4. Revision of the Unstable Picrotoxinin Hydrolysis Product.

Review 5. Change the channel: CysLoop receptor antagonists from nature.

Review 7. Modern synthetic efforts toward biologically active terpenes.

Review 1. GABAA receptors: structure, function, pharmacology, and related disorders.

Review 2. Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis.

Review 5. Change the channel: CysLoop receptor antagonists from nature.

Review 1. GABA_A receptors: structure, function, pharmacology, and related disorders.