Literature DB >> 21526254

Cascade polycyclisations in natural product synthesis.

Edward A Anderson1.   

Abstract

The efficient, stereocontrolled construction of polycyclic ring systems has long presented a formidable challenge to synthetic chemists. Cascade reactions offer a 'quick fix'--building multiple rings in a single step--and often dramatically shorten a synthetic route. In this Emerging Area article, a selection of the most recent and impressive examples of applications of this tactic to natural product synthesis are discussed, which demonstrate the ambition and achievements of the modern synthetic chemist.

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Year:  2011        PMID: 21526254     DOI: 10.1039/c1ob05212h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  10 in total

1.  Hydroxyl-substituted ladder polyethers via selective tandem epoxidation/cyclization sequence.

Authors:  Lara C Czabaniuk; Timothy F Jamison
Journal:  Org Lett       Date:  2015-02-03       Impact factor: 6.005

Review 2.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

3.  Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.

Authors:  Nihan Çelebi-Ölçüm; Yu-hong Lam; Edward Richmond; Kenneth B Ling; Andrew D Smith; Kendall N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-04       Impact factor: 15.336

4.  A dioxane template for highly selective epoxy alcohol cyclizations.

Authors:  James J Mousseau; Christopher J Morten; Timothy F Jamison
Journal:  Chemistry       Date:  2013-06-17       Impact factor: 5.236

5.  Cascade approach to stereoselective polycyclic ether formation: epoxides as trapping agents in the transposition of allylic alcohols.

Authors:  Youwei Xie; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-22       Impact factor: 15.336

6.  Ynamide carbopalladation: a flexible route to mono-, bi- and tricyclic azacycles.

Authors:  Craig D Campbell; Rebecca L Greenaway; Oliver T Holton; P Ross Walker; Helen A Chapman; C Adam Russell; Greg Carr; Amber L Thomson; Edward A Anderson
Journal:  Chemistry       Date:  2015-07-16       Impact factor: 5.236

7.  Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors:  Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal:  Chem Sci       Date:  2017-01-30       Impact factor: 9.825

8.  Synthesis of Some Novel Fused Pyrimido[4″,5″:5',6']-[1,2,4]triazino[3',4':3,4] [1,2,4]triazino[5,6-b]indoles with Expected Anticancer Activity.

Authors:  Rania S Ali; Hosam A Saad
Journal:  Molecules       Date:  2018-03-19       Impact factor: 4.411

9.  Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials.

Authors:  Martin Kamlar; August Runemark; Ivana Císařová; Henrik Sundén
Journal:  Org Lett       Date:  2020-10-20       Impact factor: 6.005

10.  Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.

Authors:  Rebecca E Ruscoe; Neal J Fazakerley; Huanming Huang; Sabine Flitsch; David J Procter
Journal:  Chemistry       Date:  2015-11-26       Impact factor: 5.236

  10 in total

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