Literature DB >> 14572247

Concise synthesis of the chemopreventitive agent (+/-)-deguelin via a key 6-endo hydroarylation.

Stefan J Pastine1, Dalibor Sames.   

Abstract

[reaction: see text]. A concise total synthesis of (+/-)-deguelin was achieved with a longest linear sequence of six steps in 68% yield. A key step was the platinum-catalyzed 6-endo hydroarylation of an alkynone intermediate.

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Year:  2003        PMID： 14572247     DOI： 10.1021/ol035419j

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


  6 in total

1.  Concise modular asymmetric synthesis of deguelin, tephrosin and investigation into their mode of action.

Authors:  José Garcia; Sofia Barluenga; Kristin Beebe; Len Neckers; Nicolas Winssinger
Journal:  Chemistry       Date:  2010-08-23       Impact factor: 5.236

2.  Catalytic coupling of arene C-H bonds and alkynes for the synthesis of coumarins: substrate scope and application to the development of neuroimaging agents.

Authors:  Paul A Vadola; Dalibor Sames
Journal:  J Org Chem       Date:  2012-07-06       Impact factor: 4.354

3.  C-H bond functionalization via hydride transfer: direct coupling of unactivated alkynes and sp(3) C-H bonds catalyzed by platinum tetraiodide.

Authors:  Paul A Vadola; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2009-11-18       Impact factor: 15.419

4.  A Concise Enantioselective Synthesis and Cytotoxic Evaluation of the Anticancer Rotenoid Deguelin Enabled by a Tandem Knoevenagel/Conjugate Addition/Decarboxylation Sequence.

Authors:  Rebecca L Farmer; Karl A Scheidt
Journal:  Chem Sci       Date:  2013-08       Impact factor: 9.825

5.  Stereocontrolled semi-syntheses of deguelin and tephrosin.

Authors:  David A Russell; Julien J Freudenreich; Joe J Ciardiello; Hannah F Sore; David R Spring
Journal:  Org Biomol Chem       Date:  2017-01-30       Impact factor: 3.876

6.  Asymmetric Gold(I)-Catalyzed Tandem Hydroarylation-Nazarov Cyclization: Enantioselective Access to Cyclopentenones.

Authors:  Marta Solas; Samuel Suárez-Pantiga; Roberto Sanz
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-18       Impact factor: 16.823
  6 in total

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