Evolution of multi-component anion relay chemistry (ARC): construction of architecturally complex natural and unnatural products

Efficient construction of architecturally complex natural and unnatural products is the hallmark of organic chemistry. Anion relay chemistry (ARC)-a multi-component coupling protocol-has the potential to provide the chemist with a powerful synthetic tactic, enabling efficient, rapid elaboration of s...

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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 45; pp. 5883 - 5895
Main Authors Smith, 3rd, Amos B, Wuest, William M
Format Journal Article
LanguageEnglish
Published England 01.01.2008
Subjects
Acetonitriles - chemical synthesis
Acetonitriles - chemistry
Acrolein - chemical synthesis
Acrolein - chemistry
Anions - chemistry
Benzaldehydes - chemical synthesis
Benzaldehydes - chemistry
Bryostatins - chemical synthesis
Bryostatins - chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Indolizidines - chemical synthesis
Indolizidines - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Quinolizines - chemical synthesis
Quinolizines - chemistry
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Spiro Compounds
Stereoisomerism
Sulfur Compounds - chemical synthesis
Sulfur Compounds - chemistry
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Summary:Efficient construction of architecturally complex natural and unnatural products is the hallmark of organic chemistry. Anion relay chemistry (ARC)-a multi-component coupling protocol-has the potential to provide the chemist with a powerful synthetic tactic, enabling efficient, rapid elaboration of structurally complex scaffolds in a single operation with precise stereochemical control. The ARC tactic can be subdivided into two main classes, comprising the relay of negative charge either through bonds or through space, the latter with aid of a transfer agent. This review will present the current state of through-space anion relay, in conjunction with examples of natural and unnatural product syntheses that illustrate the utility of this synthetic method.
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Amos B. Smith, III received a B.S.-M.S. degree in chemistry from Bucknell University and a Ph.D. from The Rockefeller University. After a postdoctoral year at Rockefeller, he joined the Chemistry Department at the University of Pennsylvania; currently he is the Rhodes-Thompson Professor of Chemistry, the Associate Director of the Penn Center for Molecular Discovery, and the inaugural Editor-in-Chief of Organic Letters. From 1988-1996 he served as Chair of the Department. His research interests, recorded in over 500 articles, include organic synthesis, particularly the synthesis of architecturally complex bioactive natural products, bioorganic chemistry and materials science.
Dedicated to Professor Andrew B. Holmes, friend, editorial colleague, and chemist/scholar extraordinaire on the occasion of his 65th birthday.
Fax: 1-(215) 898-5129; Tel: 1-(215) 898-4860; E-mail: smithab@sas.upenn.edu
William M. Wuest received a B.S. degree in chemistry/business from the University of Notre Dame in 2003, and a Ph.D. in chemistry from the University of Pennsylvania with Prof. Amos B. Smith, III in 2008. He is now working as a postdoctoral researcher with Prof. Christopher T. Walsh at Harvard Medical School. His current research is concerned with the combinatorial biosynthesis of architecturally diverse nonproteinogenic amino acids and peptide natural products.
ISSN:1359-7345
1364-548X
DOI:10.1039/b810394a