title: Evolution of multi-component anion relay chemistry (ARC): construction of architecturally complex natural and unnatural products.
abstract: 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.
authors.affiliation: Department of Chemistry, Penn Center for Molecular Discovery, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
authors.forename: William M
authors.initials: WM
authors.lastname: Wuest
mesh_terms: D000097:Acetonitriles / Q000138:chemical synthesis / Q000737:chemistry; D000171:Acrolein / Q000138:chemical synthesis / Q000737:chemistry; D000838:Anions / Q000737:chemistry*; D001547:Benzaldehydes / Q000138:chemical synthesis / Q000737:chemistry; D054713:Bryostatins / Q000138:chemical synthesis / Q000737:chemistry; D002625:Chemistry, Organic; D020650:Combinatorial Chemistry Techniques; D054836:Indolizidines / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry; D013141:Spiro Compounds; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry; D000095702:Polyether Toxins
chemical_list: D000097:Acetonitriles; D000171:Acrolein; D000838:Anions; D001547:Benzaldehydes; D054713:Bryostatins; D054836:Indolizidines; D018942:Macrolides; D011807:Quinolizines; D012717:Sesquiterpenes; D013141:Spiro Compounds; D013457:Sulfur Compounds; C438055:dithiane; C410430:mycoticin A; C475125:spirastrellolide A; C083856:spongistatin 1; D000095702:Polyether Toxins; C046785:bryostatin 1; C032175:benzaldehyde; C032159:acetonitrile