Literature DB >> 12375933

An acid-catalyzed macrolactonization protocol.

Barry M Trost1, John D Chisholm.   

Abstract

[reaction: see text] An efficient macrolactonization protocol devoid of any base was developed derived from the use of vinyl esters in transesterification. Subjecting a hydroxy acid and ethoxyacetylene to 2 mol % [RuCl(2)(p-cymene)](2) in toluene followed by addition of camphorsulfonic acid or inverse addition provided macrolactones in good yields.

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Year:  2002        PMID: 12375933     DOI: 10.1021/ol026726c

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


  5 in total

1.  Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P.

Authors:  Barry M Trost; Julien P N Papillon; Thomas Nussbaumer
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

2.  Asymmetric catalytic alkynylation of acetaldehyde: application to the synthesis of (+)-tetrahydropyrenophorol.

Authors:  Barry M Trost; Adrien Quintard
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-05       Impact factor: 15.336

3.  Total synthesis and stereochemical assignment of (-)-ushikulide A.

Authors:  Barry M Trost; Brendan M O'Boyle; Daniel Hund
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

4.  Exploiting orthogonally reactive functionality: synthesis and stereochemical assignment of (-)-ushikulide A.

Authors:  Barry M Trost; Brendan M O'Boyle
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

5.  Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

Authors:  Porino Va; William R Roush
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

  5 in total

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