Literature DB >> 16805562

Cross metathesis as a general strategy for the synthesis of prostacyclin and prostaglandin analogues.

Neil A Sheddan1, Johann Mulzer.   

Abstract

[reaction: see text] A cross metathesis (CM) approach has been successfully applied to introduce fully functionalized omega-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses of isocarbacyclin, 15R-TIC, carbacyclin, and PGF(2)(alpha) and the formal syntheses of 15-deoxy-TIC and PGJ(2).

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Year:  2006        PMID： 16805562     DOI： 10.1021/ol061141u

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


  7 in total

1.  A chiral Lewis acid strategy for enantioselective allylic C-H oxidation.

Authors:  Dustin J Covell; M Christina White
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Synthesis of caeliferins, elicitors of plant immune responses: accessing lipophilic natural products via cross metathesis.

Authors:  Inish O'Doherty; Joshua J Yim; Eric A Schmelz; Frank C Schroeder
Journal:  Org Lett       Date:  2011-10-12       Impact factor: 6.005

3.  Concise, scalable and enantioselective total synthesis of prostaglandins.

Authors:  Fuhao Zhang; Jingwen Zeng; Mohan Gao; Linzhou Wang; Gen-Qiang Chen; Yixin Lu; Xumu Zhang
Journal:  Nat Chem       Date:  2021-05-27       Impact factor: 24.427

4.  A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs.

Authors:  Dustin J Covell; M Christina White
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

Review 5.  Lactones in the Synthesis of Prostaglandins and Prostaglandin Analogs.

Authors:  Constantin Tănase; Lucia Pintilie; Raluca Elena Tănase
Journal:  Int J Mol Sci       Date:  2021-02-04       Impact factor: 5.923

6.  Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps.

Authors:  Graeme Coulthard; William Erb; Varinder K Aggarwal
Journal:  Nature       Date:  2012-09-13       Impact factor: 49.962

7.  Biochemical basis for the regulation of biosynthesis of antiparasitics by bacterial hormones.

Authors:  Iti Kapoor; Philip Olivares; Satish K Nair
Journal:  Elife       Date:  2020-06-08       Impact factor: 8.140
  7 in total

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