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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

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

Key words

macrocyclization - dehydromuscone - Grela’s catalyst - fragrances - ring-closing metathesis - macrocycles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1932-9317.
  • Supporting Information


Publication History

Received: 05 August 2022

Accepted after revision: 29 August 2022

Accepted Manuscript online:
29 August 2022

Article published online:
12 October 2022

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