Recent Advances in the Benzannulation of Substituted 3‐Alkoxycarbonyl‐3,5‐hexadienoic Acids and 3‐Alkoxycarbonylhex‐3‐en‐5‐ynoic Acids to Polysubstituted Aromatics
- 7 August 2007
- journal article
- Published by Wiley in Chemistry – A European Journal
- Vol. 13 (24), 6782-6791
- https://doi.org/10.1002/chem.200700735
Abstract
The benzannulation reactions of substituted 3‐alkoxycarbonyl‐3,5‐hexadienoic and 3‐alkoxycarbonylhex‐3‐en‐5‐ynoic acids offer a straightforward access to various polysubstituted aromatic compounds. The process is very flexible, and can be applied to the regiospecific preparation of oligoaryls, naphthalenes, ring‐fused heterocycles, chiral tetrahydronaphthalenes, C‐aryl‐glycosides and many natural products of different structure. In this Concept article, we highlight the potential of this annulation reaction by illustration of our recent contribution to this field, as well as the studies previous reported by others.Keywords
This publication has 68 references indexed in Scilit:
- The First Century of Ketenes (1905–2005): The Birth of a Versatile Family of Reactive IntermediatesAngewandte Chemie-International Edition, 2005
- A New Preparative Route to Substituted Dibenzofurans by Benzannulation Reaction. An Application to the Synthesis of CannabifuranSynlett, 2003
- [3+3]‐Cyclisierungsreaktionen von 1,3‐Bis‐Silylenolethern mit 1,1‐Diacetylcyclopentan und 1,1‐DiacetylcyclopropanAngewandte Chemie, 2003
- A Concise Synthesis of 3-Hydroxy-4-(β-glucopyranosyl) Benzoate: A New Route to β-C-Aryl GlycosidesSynlett, 1999
- A New Enantioselective Route to Bisabolane Sesquiterpenes Phenols: Synthesis of (S)-(+)-Curcuphenol and (S)-(+)-CurcumeneSynlett, 1998
- Aromatic Annulation of Alicyclic α,β-Unsaturated Aldehydes: Synthesis of Chirally Substituted TetrahydronaphthalenesSynlett, 1998
- 1,6-Electrocyclic reactionsRussian Chemical Reviews, 1995
- Inverse electron demand Diels-Alder reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of oxygenated aromatics: benzene, phenol, catechol, resorcinol, and pyrogallol annulation. Regiospecific total synthesis of sendaverine and a preparation of 6,7-benzomorphansThe Journal of Organic Chemistry, 1984
- The Stobbe condensation. Part VIII. The cyclisation of trans-3-methoxycarbonyl-4-(2-thienyl)but-3-enoic acid and αβ-dithenylidene-succinic anhydride to the corresponding benzothiophen derivativesJournal of the Chemical Society C: Organic, 1971
- 208. The Stobbne condensation. Part I. The cyclisation of methyl hydrogen cis-γ-o-methoxyphenyl- and Methyl Hydrogen cis-γ-p-methoxyphenyl-itaconate to the corresponding naphthalene derivativesJournal of the Chemical Society, 1959