Literature DB >> 19827755

An efficient synthetic approach to polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones.

Cristian Draghici1, Qiufeng Huang, Matthias Brewer.   

Abstract

A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic gamma-silyloxy-beta-hydroxy-alpha-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.

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Year:  2009        PMID： 19827755     DOI： 10.1021/jo901978y

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  Synthesis of demissidine by a ring fragmentation 1,3-dipolar cycloaddition approach.

Authors:  Zhe Zhang; Geoffrey M Giampa; Cristian Draghici; Qiufeng Huang; Matthias Brewer
Journal:  Org Lett       Date:  2013-04-15       Impact factor: 6.005

2.  Stereoelectronic effects in the fragmentation of γ-silyloxy-β-hydroxy-α-diazocarbonyl compounds.

Authors:  Nitinkumar D Jabre; Matthias Brewer
Journal:  J Org Chem       Date:  2012-10-15       Impact factor: 4.354

3.  Formal and total synthesis of (±)-cycloclavine.

Authors:  Nitinkumar D Jabre; Teruki Watanabe; Matthias Brewer
Journal:  Tetrahedron Lett       Date:  2014-01-01       Impact factor: 2.415

4.  A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.

Authors:  Geoffrey M Giampa; Jian Fang; Matthias Brewer
Journal:  Org Lett       Date:  2016-08-08       Impact factor: 6.005
  4 in total

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