Literature DB >> 17455940

Application of the intramolecular Yamamoto vinylogous aldol reaction to the synthesis of macrolides.

Joseph A Abramite1, Tarek Sammakia.   

Abstract

An intramolecular version of the Yamamoto vinylogous aldol reaction, a method that employs the bulky Lewis acid ATPH to control the site of aldolization, is described. This macrocyclization process is effective for the construction of 10-, 12-, and 14-membered macrolides. The yields are high (70-90%), and the reaction can proceed with excellent remote stereocontrol (dr > or = 20:1) with chiral substrates.

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Year:  2007        PMID： 17455940     DOI： 10.1021/ol0704901

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


  3 in total

1.  Toward the synthesis of (+)-peloruside A via an intramolecular vinylogous aldol reaction.

Authors:  Jeffrey A Gazaille; Joseph A Abramite; Tarek Sammakia
Journal:  Org Lett       Date:  2011-12-12       Impact factor: 6.005

2.  The vinylogous aldol reaction of unsaturated esters and enolizable aldehydes using the novel Lewis acid aluminum tris(2,6-di-2-naphthylphenoxide).

Authors:  Jeffrey A Gazaille; Tarek Sammakia
Journal:  Org Lett       Date:  2012-05-23       Impact factor: 6.005

3.  Tuning the Stereoselectivity of an Intramolecular Aldol Reaction by Precisely Modifying a Metal-Organic Framework Catalyst.

Authors:  Joel Cornelio; Shane G Telfer
Journal:  Chem Asian J       Date:  2022-05-23
  3 in total

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