Literature DB >> 22679931

A reductive-Heck approach to the hydroazulene ring system: a formal synthesis of the englerins.

Peng Gao1, Silas P Cook.   

Abstract

The reduction of a palladium enolate prior to β-hydride elimination provides a unique reaction for the synthesis of the hydroazulene ring system. When combined with a transannular epoxide rearrangement cascade, the reductive-Heck reaction allows rapid entry to the oxo-bridged guaiane core of the englerins.

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Year:  2012        PMID： 22679931     DOI： 10.1021/ol3013167

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


  10 in total

Review 1.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

Review 2.  Englerins: A Comprehensive Review.

Authors:  Zhenhua Wu; Senzhi Zhao; David M Fash; Zhenwu Li; William J Chain; John A Beutler
Journal:  J Nat Prod       Date:  2017-02-07       Impact factor: 4.050

3.  Palladium-Catalyzed Reductive Heck Coupling of Alkenes.

Authors:  Lucas J Oxtoby; John A Gurak; Steven R Wisniewski; Martin D Eastgate; Keary M Engle
Journal:  Trends Chem       Date:  2019-06-20

4.  Synthesis of highly functionalized tri- and tetrasubstituted alkenes via Pd-catalyzed 1,2-hydrovinylation of terminal 1,3-dienes.

Authors:  Vaneet Saini; Mark O'Dair; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-01-06       Impact factor: 15.419

5.  Quadruple C-H activation coupled to hydrofunctionalization and C-H silylation/borylation enabled by weakly coordinated palladium catalyst.

Authors:  Bo-Cheng Tang; Wen-Xuan Lin; Xiang-Long Chen; Cai He; Jin-Tian Ma; Yan-Dong Wu; Yu Lan; An-Xin Wu
Journal:  Nat Commun       Date:  2020-11-09       Impact factor: 14.919

6.  Assembly of Complex 1,4-Cycloheptadienes by (4+3) Cycloaddition of Rhodium(II) and Gold(I) Non-Acceptor Carbenes.

Authors:  Helena Armengol-Relats; Mauro Mato; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-24       Impact factor: 15.336

7.  Intramolecular carbonickelation of alkenes.

Authors:  Rudy Lhermet; Muriel Durandetti; Jacques Maddaluno
Journal:  Beilstein J Org Chem       Date:  2013-04-12       Impact factor: 2.883

8.  Total synthesis of (+)-linoxepin by utilizing the Catellani reaction.

Authors:  Harald Weinstabl; Marcel Suhartono; Zafar Qureshi; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-16       Impact factor: 15.336

9.  Endo-selective Pd-catalyzed silyl methyl Heck reaction.

Authors:  Marvin Parasram; Viktor O Iaroshenko; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2014-12-17       Impact factor: 15.419

10.  Synthesis and Biological Evaluation of New (-)-Englerin Analogues.

Authors:  Laura López-Suárez; Lorena Riesgo; Fernando Bravo; Tanya T Ransom; John A Beutler; Antonio M Echavarren
Journal:  ChemMedChem       Date:  2016-03-23       Impact factor: 3.466
  10 in total

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