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Literature DB >> 17638376

Ring-rearrangement metathesis.

Abstract

Ring-rearrangement metathesis (RRM) refers to the combination of several metathesis transformations into a domino process, in which an endocyclic double bond of a cycloolefin reacts with an exocyclic alkene. RRM has proven to be a powerful method for the rapid construction of complex structures. The extension of the basic ring-opening-ring-closing metathesis process by further metathesis steps as well as an examination of the driving forces, limits, scope, recent advantages, and future perspectives of these domino sequences is presented with various examples, thus reflecting the high efficiency and utility of RRM in organic synthesis.

Entities: Chemical

Year: 2007 PMID： 17638376 DOI： 10.1002/asia.200700072

Source DB: PubMed Journal: Chem Asian J ISSN： 1861-471X

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Cited

17 in total

Review 1. Recent advances in the chemistry and biology of naturally occurring antibiotics.

Authors: K C Nicolaou; Jason S Chen; David J Edmonds; Anthony A Estrada
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

2. Studies on an (S)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptor antagonist IKM-159: asymmetric synthesis, neuroactivity, and structural characterization.

Authors: Lina Juknaitė; Yutaro Sugamata; Kazuya Tokiwa; Yuichi Ishikawa; Satoshi Takamizawa; Andrew Eng; Ryuichi Sakai; Darryl S Pickering; Karla Frydenvang; Geoffrey T Swanson; Jette S Kastrup; Masato Oikawa
Journal: J Med Chem Date: 2013-03-13 Impact factor: 7.446

3. Computation and experiment reveal that the ring-rearrangement metathesis of Himbert cycloadducts can be subject to kinetic or thermodynamic control.

Authors: Jonathan K Lam; Hung V Pham; K N Houk; Christopher D Vanderwal
Journal: J Am Chem Soc Date: 2013-11-06 Impact factor: 15.419

4. Regioselective Domino Metathesis of Unsymmetrical 7-Oxanorbornenes with Electron-Rich Vinyl Acetate toward Biologically Active Glutamate Analogues.

Authors: Masato Oikawa; Minoru Ikoma; Makoto Sasaki; Martin B Gill; Geoffrey T Swanson; Keiko Shimamoto; Ryuichi Sakai
Journal: European J Org Chem Date: 2009-11-01

5. Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues.

Authors: Minoru Ikoma; Masato Oikawa; Martin B Gill; Geoffrey T Swanson; Ryuichi Sakai; Keiko Shimamoto; Makoto Sasaki
Journal: European J Org Chem Date: 2008-11

10. Stereochemistry of ring-opening/cross metathesis reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitriles with allyl alcohol and allyl acetate.

Authors: Piotr Wałejko; Michał Dąbrowski; Lech Szczepaniak; Jacek W Morzycki; Stanisław Witkowski
Journal: Beilstein J Org Chem Date: 2015-10-13 Impact factor: 2.883

Ring-rearrangement metathesis.

Review 1. Recent advances in the chemistry and biology of naturally occurring antibiotics.

2. Studies on an (S)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptor antagonist IKM-159: asymmetric synthesis, neuroactivity, and structural characterization.

3. Computation and experiment reveal that the ring-rearrangement metathesis of Himbert cycloadducts can be subject to kinetic or thermodynamic control.

4. Regioselective Domino Metathesis of Unsymmetrical 7-Oxanorbornenes with Electron-Rich Vinyl Acetate toward Biologically Active Glutamate Analogues.

5. Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues.

6. From nature to the laboratory and into the clinic.

7. Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps.

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

9. Design and synthesis of fused polycycles via Diels-Alder reaction and ring-rearrangement metathesis as key steps.

10. Stereochemistry of ring-opening/cross metathesis reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitriles with allyl alcohol and allyl acetate.