New methodologies towards lactones and methylene-lactones : application to the total synthesis of Polycavernoside A.

by Dumeunier, Raphaël

Abstract (Summary)
Methylene-butyrolactones are readily accessed by two methodologies based on a particular ene reaction. Both methodologies have been applied to the synthesis of the northern fragment of Polycavernoside. A reverse Julia reaction was used as the key step of a new methodology towards triene frameworks ; a mechanistic study revealed the unexpected role of triflic acid in the field of metal triflates catalysed acylation of alcohols, and a new tandem Brook rearrangement-allylation sequence was developed in the viewpoint of an improved total synthesis of Polycavernoside A.
Bibliographical Information:


School:Université catholique de Louvain

School Location:Belgium

Source Type:Master's Thesis

Keywords:ene allylation julia brook silicon shift


Date of Publication:06/04/2004

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