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Literature DB >> 32149511

Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine.

Renyu Guo¹, Brittany P Witherspoon¹, M Kevin Brown¹.

Abstract

The first enantioselective synthesis of (-)-cajanusine is presented. Key features of the route include a rapid synthesis of the [4.2.0]bicyclooctane core by an enantioselective isomerization/stereoselective [2+2]-cycloaddition strategy as well as prominent use of catalytic methods for bond construction. The evolution of the approach is also presented that highlights unexpected roadblocks and how novel solutions were developed.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2020 PMID： 32149511 PMCID： PMC7252469 DOI： 10.1021/jacs.0c00359

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

28 in total

1. Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

Authors: Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal: J Am Chem Soc Date: 2018-11-05 Impact factor: 15.419

2. Catalytic enantioselective allenoate-alkene [2 + 2] cycloadditions.

Authors: Michael L Conner; Yao Xu; M Kevin Brown
Journal: J Am Chem Soc Date: 2015-03-10 Impact factor: 15.419

3. Tandem Decarboxylative Cyclization/Alkenylation Strategy for Total Syntheses of (+)-Longirabdiol, (-)-Longirabdolactone, and (-)-Effusin.

Authors: Jianpeng Zhang; Zijian Li; Junming Zhuo; Yue Cui; Ting Han; Chao Li
Journal: J Am Chem Soc Date: 2019-05-14 Impact factor: 15.419

4. Acid-catalyzed intramolecular [2+2] cycloaddition of ene-allenones: facile access to bicyclo[n.2.0] frameworks.

Authors: Jun-Feng Zhao; Teck-Peng Loh
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

5. Oxidation of silyl enol ethers by using IBX and IBX.N-oxide complexes: a mild and selective reaction for the synthesis of enones.

Authors: K C Nicolaou; David L F Gray; Tamsyn Montagnon; Scott T Harrison
Journal: Angew Chem Int Ed Engl Date: 2002-03-15 Impact factor: 15.336

6. Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates.

Authors: Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2018-03-24 Impact factor: 15.336

Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine.

1. Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

2. Catalytic enantioselective allenoate-alkene [2 + 2] cycloadditions.

3. Tandem Decarboxylative Cyclization/Alkenylation Strategy for Total Syntheses of (+)-Longirabdiol, (-)-Longirabdolactone, and (-)-Effusin.

4. Acid-catalyzed intramolecular [2+2] cycloaddition of ene-allenones: facile access to bicyclo[n.2.0] frameworks.

5. Oxidation of silyl enol ethers by using IBX and IBX.N-oxide complexes: a mild and selective reaction for the synthesis of enones.

6. Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates.

7. Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis.

8. Quaternary-centre-guided synthesis of complex polycyclic terpenes.

9. A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A.

10. Redox-Active Esters in Fe-Catalyzed C-C Coupling.

1. Enantioselective Synthesis of (+)-Hippolide J and Reevaluation of Antifungal Activity.