Direct Synthesis of Stereodefined and Functionalized Dienes as Valuable Building Blocks

Authors

  • Nuno Maulide University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria. nuno.maulide@univie.ac.at
  • Caroline Souris University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria
  • Frédéric Frébault University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria
  • Marco Luparia University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria
  • Davide Audisio University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria

DOI:

https://doi.org/10.2533/chimia.2014.248

Keywords:

Allylic alkylation, Azide, Diene, Inthomycin c, Ring opening

Abstract

We have reported a direct and stereoselective synthesis of functionalized dienoic carboxylates from the simple bicyclic lactone 1. The use of oxygen- or nitrogen-based nucleophiles in a domino allylic alkylation/4?-electrocyclic ring opening affords reliable access to dienes with interesting functionalities. Alternatively, halide substitution offers synthesis of other classes of functionalized dienoic acids. Herein, we demonstrate the utility of such dienoic products as key building blocks in various transformations as well as natural product synthesis.

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Published

2014-04-30

How to Cite

[1]
N. Maulide, C. Souris, F. Frébault, M. Luparia, D. Audisio, Chimia 2014, 68, 248, DOI: 10.2533/chimia.2014.248.