Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5225099 | Tetrahedron | 2008 | 8 Pages |
Abstract
The RuO4-catalyzed oxidative polycyclization of digeranyl, a Cs-symmetric tetraene possessing a repetitive 1,5-diene structural motif, has been studied. The required substrate has been synthesized by Ti(III)-mediated tail-to-tail homocoupling of geranyl bromide. The process afforded two hitherto unknown isomeric tris-tetrahydrofuran products possessing unexpected all-threo cis-trans-cis and cis-trans-trans relative configuration. The new stereochemical outcome is explained based on previously formulated chelation or steric control models on the basis of structural differences between digeranyl and previously studied isoprenoid polyenes farnesyl acetate, geranylgeranyl acetate and squalene.
Graphical abstractDownload full-size image
Keywords
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Vincenzo Piccialli, Nicola Borbone, Giorgia Oliviero,