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Preparation of Musk‐Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination
Author(s) -
Sytniczuk Adrian,
Leszczyńska Agnieszka,
Kajetanowicz Anna,
Grela Karol
Publication year - 2018
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201801463
Subject(s) - ring closing metathesis , metathesis , chemistry , yield (engineering) , substrate (aquarium) , ring (chemistry) , diene , oleic acid , double bond , organic chemistry , stereochemistry , combinatorial chemistry , biology , materials science , biochemistry , natural rubber , metallurgy , polymerization , polymer , ecology
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.