Improvements towards the synthesis of phormidolides B and C

Authors

  • Alejandro Gil Universitat de Barcelona. Parc Científic de Barcelona. ChemBioLab
  • Fernando Albericio Universitat de Barcelona. Parc Científic de Barcelona. ChemBioLab
  • Mercedes Álvarez Universitat de Barcelona. Parc Científic de Barcelona. ChemBioLab

Keywords:

Total synthesis, natural products, diastereoselectivity, phormidolide.

Abstract

This paper describes the most important optimization carried out in the phormidolides B and C synthetic process. It consists in a change of strategy in order to synthesize the macrocyclic core of this family of compounds. The main changes have been the use of a diastereoselective methodology to construct the tetrahydrofuran (THF) core, a (Z)–1,5–anti allylstannane addition where the synthesis converges, and a notable improvement in the cyclization conditions. All this work has supposed a 10-fold increment in the overall yield of the synthesis.

Keywords: Total synthesis, natural products, diastereoselectivity, phormidolide.

Downloads

Download data is not yet available.

Downloads

Issue

No. 15 (2016)

Section

Articles

License

The intellectual property of articles belongs to the respective authors.

On submitting articles for publication to the journal Revista de la Societat Catalana de Química, authors accept the following terms:

  1. Authors assign to Catalan Society of Chemistry (a subsidiary of Institut d’Estudis Catalans) the rights of reproduction, communication to the public and distribution of the articles submitted for publication to Revista de la Societat Catalana de Química.
  2. Authors answer to Catalan Society of Chemistry for the authorship and originality of submitted articles.
  3. Authors are responsible for obtaining permission for the reproduction of all graphic material included in articles.
  4. Catalan Society of Chemistry declines all liability for the possible infringement of intellectual property rights by authors.
  5. The contents published in the journal, unless otherwise stated in the text or in the graphic material, are subject to a Creative Commons Attribution-NonCommercial-NoDerivs (by-nc-nd) 3.0 Spain licence, the complete text of which may be found at  http://creativecommons.org/licenses/by-nc-nd/3.0/es/deed.en. Consequently, the general public is authorised to reproduce, distribute and communicate the work, provided that its authorship and the body publishing it are acknowledged, and that no commercial use and no derivative works are made of it.
  6. The journal is not responsible for the ideas and opinions expressed by the authors of the published articles.