Synlett 2022; 33(19): 1933-1937
DOI: 10.1055/a-1932-9317
letter

Synthesis of Dehydromuscone by an Alkene Metathesis Macrocyclization Reaction at 0.2 M Concentration

Authors

  • Francisco Garnes-Portolés

    a   Instituto de Tecnología Química (UPV-CSIC), Universidad Politècnica de València-Consejo Superior de Investigaciones Científicas, Avda. de los Naranjos s/n, 46022 Valencia, Spain
  • Jorge Sánchez-Quesada

    b   International Flavours & Fragrances Inc., Avda Felipe Klein 2, 12580, Benicarló, Castellón, Spain
  • Estela Espinós-Ferri

    b   International Flavours & Fragrances Inc., Avda Felipe Klein 2, 12580, Benicarló, Castellón, Spain
  • Antonio Leyva-Pérez

    a   Instituto de Tecnología Química (UPV-CSIC), Universidad Politècnica de València-Consejo Superior de Investigaciones Científicas, Avda. de los Naranjos s/n, 46022 Valencia, Spain
    b   International Flavours & Fragrances Inc., Avda Felipe Klein 2, 12580, Benicarló, Castellón, Spain

Financial support by the project PID2020-115100GB-I00 (funded by Spanish MCIINN, MCIN/AEI/10.13039/ 501100011033MICIIN) is acknowledged.


Graphical Abstract

Preview

Abstract

The industrial fragrance compound dehydromuscone was synthesized in five linear steps and 19% overall yield. The synthesis features a highly efficient nondiluted ring-closing metathesis macrocyclization reaction as a key step that proceeds at a 0.2 M concentration in the presence of 0.1 mol% Nitro-Grela catalyst. The synthesis employs commercially available linear starting materials and is shorter by at least two steps than the current industrial synthesis route.

Supporting Information



Publikationsverlauf

Eingereicht: 05. August 2022

Angenommen nach Revision: 29. August 2022

Accepted Manuscript online:
29. August 2022

Artikel online veröffentlicht:
12. Oktober 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany