Literature DB >> 19551182

Advanced approach to polycyclics by a synergistic combination of enyne metathesis and Diels-Alder reaction.

Sambasivarao Kotha1, Milind Meshram, Arti Tiwari.   

Abstract

Enyne metathesis (EM) has widely been used to prepare various synthetic and natural products. Further, a sequential use of EM and Diels-Alder (DA) reactions generates highly functionalized and intricate polycarbocycles and heterocyclic frameworks. In this critical review we describe the application of a unique combination of EM and DA reactions to prepare various amino acid derivatives, natural products and heterocycles. Some of the heterocyclic targets include cyclic peroxides, siloxanes and various nitrogen (or oxygen) containing compounds. Use of ethylene and cyclooctadiene (COD) for improving the yield of EM products are also discussed (69 references).

Entities:  

Year:  2009        PMID: 19551182     DOI: 10.1039/b810094m

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  9 in total

Review 1.  Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.

Authors:  Vaneet Saini; Benjamin J Stokes; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336

2.  Ene-yne cross-metathesis with ruthenium carbene catalysts.

Authors:  Cédric Fischmeister; Christian Bruneau
Journal:  Beilstein J Org Chem       Date:  2011-02-04       Impact factor: 2.883

3.  Tandem cross enyne metathesis (CEYM)-intramolecular Diels-Alder reaction (IMDAR). An easy entry to linear bicyclic scaffolds.

Authors:  Javier Miró; María Sánchez-Roselló; Álvaro Sanz; Fernando Rabasa; Carlos Del Pozo; Santos Fustero
Journal:  Beilstein J Org Chem       Date:  2015-08-25       Impact factor: 2.883

4.  Design and synthesis of polycyclic sulfones via Diels-Alder reaction and ring-rearrangement metathesis as key steps.

Authors:  Sambasivarao Kotha; Rama Gunta
Journal:  Beilstein J Org Chem       Date:  2015-08-06       Impact factor: 2.883

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.  Highly efficient synthesis of 3,4-diarylbutadiene sulfones using Heck-Matsuda reaction.

Authors:  Olga V Shurupova; Sergey A Rzhevskiy; Lidiya I Minaeva; Maxim A Topchiy; Andrey F Asachenko
Journal:  RSC Adv       Date:  2022-02-15       Impact factor: 3.361

7.  One-pot cross-enyne metathesis (CEYM)-Diels-Alder reaction of gem-difluoropropargylic alkynes.

Authors:  Santos Fustero; Paula Bello; Javier Miró; María Sánchez-Roselló; Günter Haufe; Carlos Del Pozo
Journal:  Beilstein J Org Chem       Date:  2013-11-28       Impact factor: 2.883

8.  Design and synthesis of propellane derivatives and oxa-bowls via ring-rearrangement metathesis as a key step.

Authors:  Sambasivarao Kotha; Rama Gunta
Journal:  Beilstein J Org Chem       Date:  2015-09-24       Impact factor: 2.883

Review 9.  Diversity-Oriented Approaches to Polycycles and Heterocycles via Enyne Metathesis and Diels-Alder Reaction as Key Steps.

Authors:  Sambasivarao Kotha; Arjun S Chavan; Deepti Goyal
Journal:  ACS Omega       Date:  2019-12-16
  9 in total

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