Skip to Main content Skip to Navigation
Theses

Acylations radicalaires diastéréocontrôlées : application à la synthèse de tétrahydrofuranes et pyrrolidines polysubstitués

Abstract : This thesis describes a new access to the 2,3,5-trisubstituted tetrahydrofuran moiety. This strategy includes as a first step an addition of an acylradical on to an activated olefin (Baylis-Hillman adduct), followed by a reductive cyclization of the corresponding 1,4-keto-alcohol. High levels of 1,2- and 1,3-stereocontrol were attained using, in these two steps, tris(trimethylsilyl)silane as an hydrogen transfer agent. This methodology was then applied to the synthesis of the Gymnodimine THF fragment and to the first total synthesis of a tricyclic naturalcompound : no.2106A. Finally, the use of aza-Baylis-Hillman adducts led to an efficient access to nitrogen analogues, including pyrrolidines and bicyclic compounds such as indolizidinones or pyrrolizidines.
Document type :
Theses
Complete list of metadatas

Cited literature [319 references]  Display  Hide  Download

https://tel.archives-ouvertes.fr/tel-02003495
Contributor : Abes Star :  Contact
Submitted on : Friday, February 1, 2019 - 12:05:45 PM
Last modification on : Wednesday, April 10, 2019 - 6:15:06 PM
Long-term archiving on: : Thursday, May 2, 2019 - 6:03:55 PM

File

GRELAUD_SIMON_2016.pdf
Version validated by the jury (STAR)

Identifiers

  • HAL Id : tel-02003495, version 1

Collections

Citation

Simon Grélaud. Acylations radicalaires diastéréocontrôlées : application à la synthèse de tétrahydrofuranes et pyrrolidines polysubstitués. Chimie organique. Université de Bordeaux, 2016. Français. ⟨NNT : 2016BORD0313⟩. ⟨tel-02003495⟩

Share

Metrics

Record views

91

Files downloads

64