ChemInform Abstract: Chemistry of Insect Antifeedants from Azadirachta indica. Part 13. On the Use of the Intramolecular Diels-Alder Reaction for the Construction of trans-Fused Hydrobenzofuran Fragments for Azadirachtin Synthesis

Autor:	David J. Williams, Wood Anthony, Steven V. Ley, Richard N. Sheppard, Hartmuth C. Kolb, Stephen C. Smith, Alexandra M. Z. Slawin
Rok vydání:	2010
Předmět:	biology Silylation Diene Stereochemistry Substituent General Medicine Azadirachta biology.organism_classification Planarity testing chemistry.chemical_compound Azadirachtin chemistry Intramolecular force Diels–Alder reaction
Zdroj:	ChemInform. 24
ISSN:	0931-7597
Popis:	This paper describes a detailed analysis of the influence of various substituents on the stereochemical outcome of the intramolecular Diels–Alder cyclisation of a number of ether-linked trienes. In particular, the role of diene planarity in governing reaction synchronicity and related twist asynchronicity is delineated. Additionally, the controlling influence of a large dimethyl(phenyl)silyl substituent on the dienophile portion of the triene is also explored. A detailed transition-state analysis is given together with X-ray structures for compounds 41 and 46.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::89af44eb046d8266cd953035b513f34e https://doi.org/10.1002/chin.199310283 Zobrazit plný text záznamu Plný text