Literature DB >> 17048844

Exploring skeletal diversity via ring contraction of glycal-derived scaffolds.

Adam R Yeager1, Geanna K Min, John A Porco, Scott E Schaus.   

Abstract

Aryl ether C-glycoside scaffolds have been prepared from tri-O-acetyl-D-glucal by C-glycosylation followed by allylic substitution with phenols mediated by Pd(0). The aryl ethers were subjected to either [3,3]-sigmatropic rearrangement to produce 3-pyranyl-phenols or Au(III)-mediated ring contraction to create highly substituted tetrahydrofurans. [structure: see text]

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Year:  2006        PMID: 17048844     DOI: 10.1021/ol0618252

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


  6 in total

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2.  Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold.

Authors:  Baudouin Gerard; Jean-Charles Marié; Bhaumik A Pandya; Maurice D Lee; Haibo Liu; Lisa A Marcaurelle
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4.  A unified synthetic approach to polyketides having both skeletal and stereochemical diversity.

Authors:  Shiying Shang; Hayato Iwadare; Daniel E Macks; Lisa M Ambrosini; Derek S Tan
Journal:  Org Lett       Date:  2007-04-17       Impact factor: 6.005

5.  Skeletal diversity via cationic rearrangements of substituted dihydropyrans.

Authors:  Matthew R Medeiros; Radha S Narayan; Nolan T McDougal; Scott E Schaus; John A Porco
Journal:  Org Lett       Date:  2010-07-16       Impact factor: 6.005

6.  A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes.

Authors:  Shekaraiah Devari; Manjeet Kumar; Ramesh Deshidi; Masood Rizvi; Bhahwal Ali Shah
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  6 in total

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