From Enynyl Esters to Functionalized Polycyclic Derivatives via Cycloisomerization and Post-Functionalization

Simon Guelen; Max Blazejak; Virginie Mouriès-Mansuy; Louis Fensterbank

doi:10.1055/s-0035-1561488

Synthesis, Table of Contents

Synthesis 2016; 48(19): 3199-3206
DOI: 10.1055/s-0035-1561488

paper

From Enynyl Esters to Functionalized Polycyclic Derivatives via Cycloisomerization and Post-Functionalization

Authors

Simon Guelen

Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Sorbonne Universités UPMC Univ Paris 06, 4 Place Jussieu, CC 229, 75252 Paris Cedex 05, France Email: virginie.mansuy@upmc.fr Email: louis.fensterbank@upmc.fr
Max Blazejak

Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Sorbonne Universités UPMC Univ Paris 06, 4 Place Jussieu, CC 229, 75252 Paris Cedex 05, France Email: virginie.mansuy@upmc.fr Email: louis.fensterbank@upmc.fr
Virginie Mouriès-Mansuy*

Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Sorbonne Universités UPMC Univ Paris 06, 4 Place Jussieu, CC 229, 75252 Paris Cedex 05, France Email: virginie.mansuy@upmc.fr Email: louis.fensterbank@upmc.fr
Louis Fensterbank*

Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Sorbonne Universités UPMC Univ Paris 06, 4 Place Jussieu, CC 229, 75252 Paris Cedex 05, France Email: virginie.mansuy@upmc.fr Email: louis.fensterbank@upmc.fr

Abstract

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Dedicated to Jean F. Normant with admiration

Abstract

The post-functionalization of ketone products originating from the PtCl₂-catalyzed cycloisomerization of enynyl esters is described. Post-functionalization is accomplished via diastereoselective alkylation, regioselective cyclopropane opening and regioselective Baeyer–Villiger and Beckmann rearrangements to provide functionalized polycycles.

Key words

cycloisomerization - platinum - enynyl ester - polycyclic ketone - Baeyer–Villiger - Beckmann rearrangement - lactones - lactams

Full Text

References

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Supplementary Material

Supporting Information (PDF)