Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds

ABSTRACT: The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a 1,6-double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive trisporoid family. The synthetic sequence consists of the preparation of a properly functionalized epoxygeraniol derivative, and its subsequent stereoselective cyclization mediated by Ti(III). This last step implies a domino process that starts with a homolytic epoxide opening followed by a radical cyclization and regioselective elimination. This concerted process gives access to the cyclohexane moiety with stereochemical control of five of its six carbon atoms.

• Autores: González Delgado, José Antonio; Escobar Peláez, Gustavo; Fernández Arteaga, Jesús; Fernández Barrero, Alejandro
• Tipo de recurso: Article of investigation
• Fecha de publicación: 2014
• Institución: Universidad de Antioquia
• Repositorio: Repositorio UdeA
• Idioma: eng
• OAI Identifier: oai:bibliotecadigital.udea.edu.co:10495/23689
• Acceso en línea: http://hdl.handle.net/10495/23689
• Palabra clave: Trisporoides; Apocarotenoid; Stereoselective synthesis; Reacción dominó
• Rights: openAccess
• License: http://creativecommons.org/licenses/by/2.5/co/