Literature DB >> 27198061

Metal-catalyzed cycloisomerization as a powerful tool in the synthesis of complex sesquiterpenoids.

Christos I Stathakis1, Petros L Gkizis1, Alexandros L Zografos2.   

Abstract

Covering: up to 2015Sesquiterpenoids are consistently attracting the interest of the scientific community due to their promising clinical profile as therapeutic agents. Cycloisomerization of enynes and dienes is a powerful tool in the hands of organic chemists to access them. In the last 20 years the field has witnessed remarkable advances, especially by revealing the capability of platinum and gold complexes to initiate such reactions. Nowadays, cycloisomerizations continue to enrich our knowledge with atom-economical routes and impressive cascades to reach more complex molecules. The current review covers the basic mechanistic aspects of metal catalysis in cycloisomerization reactions and their progress to the synthesis of selected complex sesquiterpenoids.

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Year:  2016        PMID: 27198061     DOI: 10.1039/c6np00026f

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  8 in total

1.  Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes.

Authors:  Patrick T Bohan; F Dean Toste
Journal:  J Am Chem Soc       Date:  2017-08-03       Impact factor: 15.419

2.  A total synthesis of (-)-Hortonone C.

Authors:  Doleshwar Niroula; Liam P Hallada; Snezna Rogelj; Rodolfo Tello-Aburto
Journal:  Tetrahedron       Date:  2016-12-11       Impact factor: 2.457

3.  Stereoselective Synthesis of Exocyclic Tetrasubstituted Vinyl Halides via Ru-Catalyzed Halotropic Cycloisomerization of 1,6-Haloenynes.

Authors:  Barry M Trost; Christopher A Kalnmals
Journal:  Org Lett       Date:  2017-04-24       Impact factor: 6.005

4.  Cyclobutene vs 1,3-Diene Formation in the Gold-Catalyzed Reaction of Alkynes with Alkenes: The Complete Mechanistic Picture.

Authors:  M Elena de Orbe; Laura Amenós; Mariia S Kirillova; Yahui Wang; Verónica López-Carrillo; Feliu Maseras; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

5.  A rhodium catalyzed cycloisomerization and tandem Diels-Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles.

Authors:  Yirong Zhou; Ali Nikbakht; Felix Bauer; Bernhard Breit
Journal:  Chem Sci       Date:  2019-04-03       Impact factor: 9.825

6.  Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step.

Authors:  Dagmar Scharnagel; Imma Escofet; Helena Armengol-Relats; M Elena de Orbe; J Nepomuk Korber; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-31       Impact factor: 15.336

7.  Iron-Catalyzed Cycloisomerization and C-C Bond Activation to Access Non-canonical Tricyclic Cyclobutanes.

Authors:  Frederik Kramm; Franziska Ullwer; Benedict Klinnert; Min Zheng; Bernd Plietker
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823

8.  Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A.

Authors:  Guilhem Chaubet; Shermin S Goh; Mujahid Mohammad; Birgit Gockel; Marie-Caroline A Cordonnier; Hannah Baars; Andrew W Phillips; Edward A Anderson
Journal:  Chemistry       Date:  2017-09-08       Impact factor: 5.236

  8 in total

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