Premium
Enantioselective synthesis of tri‐deuterated (–)‐geosmin to be used as internal standard in quantitation assays
Author(s) -
Porcelli Caterina,
Kreissl Johanna,
Steinhaus Martin
Publication year - 2020
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3874
Subject(s) - geosmin , isotopologue , chemistry , deuterium , enantioselective synthesis , flavor , combinatorial chemistry , chromatography , organic chemistry , odor , catalysis , molecule , biochemistry , physics , quantum mechanics
For the accurate and sensitive quantitation of the off‐flavor compound geosmin, particularly in complex matrices, a stable isotopologue as internal standard is highly advantageous. In this work, we present a versatile synthetic strategy leading from (4a R )‐1,4a‐dimethyl‐4,4a,5,6,7,8‐hexahydronaphthalen‐2(3 H )‐one to tri‐deuterated (–)‐geosmin ((4 S ,4a S ,8a R )‐4,8a‐dimethyl(3,3,4‐ 2 H 3 )octahydronaphthalen‐4a(2 H )‐ol). The starting material was readily accessible from inexpensive 2‐methylcyclohexan‐1‐one using previously published procedures.