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Literature DB >> 19456165

One-pot catalytic asymmetric synthesis of pyranones.

Kevin Cheng¹, Ann Rowley Kelly, Rachel A Kohn, Jessica F Dweck, Patrick J Walsh.

Abstract

Enantioenriched pyranones are important intermediates in the synthesis of natural products and the generation of compound libraries. A one-pot method for their synthesis is outlined. Catalytic asymmetric alkylation of 2-furfurals in the presence of catalytic (-)-MIB generates enantioenriched furyl zinc alkoxides. Addition of water/THF followed by NBS results in formation of pyranones with ee's >90% and yields between 46-77%.

Entities: Chemical Gene Mutation Species

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Year: 2009 PMID： 19456165 PMCID： PMC2709820 DOI： 10.1021/ol900905r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

27 in total

1. A synthesis strategy yielding skeletally diverse small molecules combinatorially.

Authors: Martin D Burke; Eric M Berger; Stuart L Schreiber
Journal: J Am Chem Soc Date: 2004-11-03 Impact factor: 15.419

2. From aryl bromides to enantioenriched benzylic alcohols in a single flask: Catalytic asymmetric arylation of aldehydes.

Authors: Jeung Gon Kim; Patrick J Walsh
Journal: Angew Chem Int Ed Engl Date: 2006-06-19 Impact factor: 15.336

3. A green chemistry approach to a more efficient asymmetric catalyst: solvent-free and highly concentrated alkyl additions to ketones.

Authors: Sang-Jin Jeon; Hongmei Li; Patrick J Walsh
Journal: J Am Chem Soc Date: 2005-11-30 Impact factor: 15.419

4. Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors: Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal: J Org Chem Date: 2006-10-27 Impact factor: 4.354

Review 3. The Increasing Value of Biomass: Moving From C6 Carbohydrates to Multifunctionalized Building Blocks via 5-(hydroxymethyl)furfural.

Authors: Konstantin I Galkin; Valentine P Ananikov
Journal: ChemistryOpen Date: 2020-11-06 Impact factor: 2.630

3 in total

One-pot catalytic asymmetric synthesis of pyranones.

1. A synthesis strategy yielding skeletally diverse small molecules combinatorially.

2. From aryl bromides to enantioenriched benzylic alcohols in a single flask: Catalytic asymmetric arylation of aldehydes.

3. A green chemistry approach to a more efficient asymmetric catalyst: solvent-free and highly concentrated alkyl additions to ketones.

4. Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

5. Highly concentrated catalytic asymmetric allylation of ketones.

6. Enantioselective syntheses of isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin.

7. De novo approach to 2-deoxy-beta-glycosides: asymmetric syntheses of digoxose and digitoxin.

8. A concise and modular synthesis of pyranicin.

9. A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides.

10. Origin of stereoselectivity in the reduction of a planar oxacarbenium.

Review 1. Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

2. Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Review 3. The Increasing Value of Biomass: Moving From C6 Carbohydrates to Multifunctionalized Building Blocks via 5-(hydroxymethyl)furfural.