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2009 Chem Soc Rev Emerging Investigator Lecture award presented
06 November 2009
Matt Gaunt was presented with the 2009 Chem Soc Rev Emerging Investigator Lecture Award at the Organic Synthesis Symposium sponsored by AstraZeneca at Loughborough University
Rapid formation of complexity in organic synthesis
28 October 2009
Chem Soc Rev issue 11 is a thematic issue illustrating the current state-of-the-art in natural product total synthesis guested edited by Huw Davies and Erik Sorensen
Green Fluorescent Protein
05 October 2009
Chem Soc Rev issue 10 is a themed issue on the topic of green fluorescent protein dedicated to the 2008 Nobel Prize winners in Chemistry, Professors Osamu Shimomura, Martin Chalfie and Roger Y. Tsien
Contents list for Chemical Society Reviews, issue 11, 2009
Front cover
Chem. Soc. Rev., 2009, 38, 2969
DOI: 10.1039/b920767h

Inside front cover
Chem. Soc. Rev., 2009, 38, 2970
DOI: 10.1039/b920768f
Contents and Highlights in Chemical Science
Chem. Soc. Rev., 2009, 38, 2971
DOI: 10.1039/b920769b
Editorial
Rapid complexity generation in natural product total synthesis
Huw M. L. Davies and Erik J. Sorensen,
Chem. Soc. Rev., 2009, 38, 2981
DOI: 10.1039/b918568m

Guest editors Huw Davies and Erik Sorensen introduce the rapid formation of molecular complexity in organic synthesis themed issue of Chemical Society Reviews.
Tutorial Reviews
Recent applications of intramolecular Diels–Alder reactions to natural product synthesis
Martin Juhl and David Tanner,
Chem. Soc. Rev., 2009, 38, 2983
DOI: 10.1039/b816703f

How can 2 × [4 + 2] = 16? 2 Sequential [4 + 2] cycloadditions (transannular Diels–Alder (TADA) reactions) = 5 (rings) + 7 (stereocentres) + 3 (C–C bonds) + 1 (C–O bond), all in a single operation!
The art of total synthesis through cascade reactions
K. C. Nicolaou and Jason S. Chen,
Chem. Soc. Rev., 2009, 38, 2993
DOI: 10.1039/b903290h

This tutorial review illustrates, with total synthesis examples, the power of cascade reactions in reaching molecular complexity with economy and elegance.
The economies of synthesis
Timothy Newhouse, Phil S. Baran and Reinhard W. Hoffmann,
Chem. Soc. Rev., 2009, 38, 3010
DOI: 10.1039/b821200g

Recession hits! The economies of synthesis are compared and contrasted with detailed examples of how efficiency was achieved.
Bond formations by intermolecular and intramolecular trappings of acylketenes and their applications in natural product synthesis
Keith P. Reber, S. David Tilley and Erik J. Sorensen,
Chem. Soc. Rev., 2009, 38, 3022
DOI: 10.1039/b912599j

Acylketenes are valuable reactive intermediates within the field of organic synthesis that facilitate the rapid construction of complex natural products.
Biogenetically inspired syntheses of alkaloid natural products
Justin Kim and Mohammad Movassaghi,
Chem. Soc. Rev., 2009, 38, 3035
DOI: 10.1039/b819925f

Biogenetic considerations and rapid functionalization of advanced molecular frameworks can allow rapid generation of molecular complexity.
Heterocycles from cyclopropanes: applications in natural product synthesis
Cheryl A. Carson and Michael A. Kerr,
Chem. Soc. Rev., 2009, 38, 3051
DOI: 10.1039/b901245c

The synthesis of natural products is as easy as 1-2-3 membered rings.
Application of donor/acceptor-carbenoids to the synthesis of natural products
Huw M. L. Davies and Justin R. Denton,
Chem. Soc. Rev., 2009, 38, 3061
DOI: 10.1039/b901170f

Highly selective rhodium carbenoids can be broadly applied to the rapid construction of natural products.
Domino reactions of rhodium(II) carbenoids for alkaloid synthesis
Albert Padwa,
Chem. Soc. Rev., 2009, 38, 3072
DOI: 10.1039/b816701j

Recent synthetic applications of the rhodium carbenoid cyclization/cycloaddition domino cascade for alkaloid synthesis.
Aromatic compounds as synthons for 1,3-dicarbonyl derivatives
Gerhard Hilt and Damian F. Weske,
Chem. Soc. Rev., 2009, 38, 3082
DOI: 10.1039/b902344p

Aromatic compounds = 1,3-dicarbonyl compounds; the equation seems odd but Birch reduction and ozonolysis make it possible.
Pericyclic domino reactions: concise approaches to natural carbocyclic frameworks
Jason Poulin, Christiane M. Grisé-Bard and Louis Barriault,
Chem. Soc. Rev., 2009, 38, 3092
DOI: 10.1039/b819798a

This tutorial review highlights new research in the area of pericyclic domino reactions. It is directed towards chemists interested in cascading reactions and the total synthesis of natural products. Concise approaches to natural frameworks are described, as well as the application of domino reactions in the context of target-oriented synthesis and total synthesis.
Enantioselective catalysis and complexity generation from allenoates
Bryan J. Cowen and Scott J. Miller,
Chem. Soc. Rev., 2009, 38, 3102
DOI: 10.1039/b816700c

Diversity-generating reactions of
-allenic esters with achiral and chiral phosphine and amine Lewis base catalysts are presented.
Applications of biotransformations and biocatalysis to complexity generation in organic synthesis
Tomas Hudlicky and Josephine W. Reed,
Chem. Soc. Rev., 2009, 38, 3117
DOI: 10.1039/b901172m

Generating downstream complexity by biological methods.
[3,3]-Sigmatropic rearrangements: recent applications in the total synthesis of natural products
Elizabeth A. Ilardi, Craig E. Stivala and Armen Zakarian,
Chem. Soc. Rev., 2009, 38, 3133
DOI: 10.1039/b901177n

A classic reaction in a modern world: recent syntheses of natural products based on [3,3]-sigmatropic rearrangements are reviewed in this article.
Multi-component cycloaddition approaches in the catalytic asymmetric synthesis of alkaloid targets
Stéphane Perreault and Tomislav Rovis,
Chem. Soc. Rev., 2009, 38, 3149
DOI: 10.1039/b816702h

In this tutorial review directed towards [n + 2 + 2] cycloadditions of heterocumulenes, alkynes and alkenes, the recent advances in the catalytic asymmetric synthesis of indolizidine, quinolizidine and azocine skeletons are discussed.
Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids
Kenneth A. Miller and Robert M. Williams,
Chem. Soc. Rev., 2009, 38, 3160
DOI: 10.1039/b816705m

Numerous creative synthetic strategies are described to access the bicyclo[2.2.2]diazaoctane core of various biologically significant prenylated indole alkaloids.
The development of endo-selective epoxide-opening cascades in water
Christopher J. Morten, Jeffery A. Byers, Aaron R. Van Dyke, Ivan Vilotijevic and Timothy F. Jamison,
Chem. Soc. Rev., 2009, 38, 3175
DOI: 10.1039/b816697h

Water promotes the efficient transformation of polyepoxy alcohols into ladder polyether structures via endo-regioselective epoxide-opening cascades.
Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling
Marisa C. Kozlowski, Barbara J. Morgan and Elizabeth C. Linton,
Chem. Soc. Rev., 2009, 38, 3193
DOI: 10.1039/b821092f

Assembly of complex chiral binaphthols by asymmetric oxidative coupling sets the stage for biomimetic natural product syntheses.
Critical Reviews
Gold and platinum catalysis—a convenient tool for generating molecular complexity
Alois Fürstner,
Chem. Soc. Rev., 2009, 38, 3208
DOI: 10.1039/b816696j

The universe of complexity-inducing reactivity that originates from the activation of
-bonds with gold or platinum catalysts can be rationalized on the basis of a unifying mechanistic framework, which is outlined in detail.
Rapid formation of complexity in the total synthesis of natural products enabled by oxabicyclo[2.2.1]heptene building blocks
Corinna S. Schindler and Erick M. Carreira,
Chem. Soc. Rev., 2009, 38, 3222
DOI: 10.1039/b915448p

The application of oxabicyclic templates has been a long standing strategy in the total synthesis of natural products to form complex systems in a limited number of synthetic transformations and from simple substrates. This review examines the reactivity of oxabicyclic building blocks and showcases their applications in total synthesis.
Transition metal-catalyzed C–H activation reactions: diastereoselectivity and enantioselectivity
Ramesh Giri, Bing-Feng Shi, Keary M. Engle, Nathan Maugel and Jin-Quan Yu,
Chem. Soc. Rev., 2009, 38, 3242
DOI: 10.1039/b816707a

Controlling the stereochemistry of transition metal-catalyzed C–H activation processes remains a tremendous challenge; this critical review discusses past and present developments towards this goal.
Back matter
Chem. Soc. Rev., 2009, 38, 3273
DOI: 10.1039/b920770h
Back cover
Chem. Soc. Rev., 2009, 38, 3275
DOI: 10.1039/b920771f




