Preparation of Musk‐Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination

• Published in: ChemSusChem Vol. 11; no. 18; pp. 3157 - 3166
• Main Authors: Sytniczuk, Adrian, Leszczyńska, Agnieszka, Kajetanowicz, Anna, Grela, Karol
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 21.09.2018
• Subjects: Biomass; Lactones; macrocyclization; Metathesis; Musk; organic synthesis; Substrates; biomass; macrocyclization; musk; metathesis; organic synthesis
• ISSN: 1864-5631; 1864-564X
• DOI: 10.1002/cssc.201801463

Macrocyclic musk belongs to a well‐known and valued class of the fragrance family. Originally, natural musks were obtained from rectal musk glands which often led to the death of the animals. Recently, a lot of effort was invested to obtain such macrocycles in a synthetic way. This research presents a study on the preparation of macrocyclic lactones with the musk scent by ring‐closing metathesis (RCM) using biomass‐derived starting materials: oleic and 9‐decenoic acid. An experimental rule correlating the C–C double bond substitution pattern in the starting diene and the yield for the RCM macrocyclization was proposed. Homogeneous catalysis: Macrocyclic lactones with the musk scent were prepared by ring‐closing metathesis (RCM) in toluene and ethyl acetate using biomass‐derived starting materials: oleic and 9‐decenoic acid (see scheme). Correlation between the C–C double bond substitution pattern in the starting diene and the yield of the RCM macrocyclization was observed.