The Jubilee of Methyl Jasmonate and Hedione®

C Chapuis - Helvetica Chimica Acta, 2012 - Wiley Online Library
An internal historical point of view is presented on the discovery and development of both
methyl jasmonate and its saturated analogue Hedione®. A discussion of the synthetic …

Methyl dihydrojasmonate and its stereoisomers: sensory properties and enantioselective analysis

P Werkhoff, G Krammer, S Brennecke… - Food Reviews …, 2002 - Taylor & Francis
Enantiomeric methyl dihydrojasmonates (MDHJs) were separated by chiral gas
chromatography (GC) and high performance liquid chromatography. Organoleptical …

Plant–Plant Signaling: Application of trans- or cis-Methyl Jasmonate Equivalent to Sagebrush Releases Does Not Elicit Direct Defenses in Native Tobacco

CA Preston, G Laue, IT Baldwin - Journal of Chemical Ecology, 2004 - Springer
Nicotiana attenuata plants growing in close proximity to damaged sagebrush (Artemisia
tridentata ssp. tridentata) suffer less herbivory than plants near undamaged sagebrush …

A new synthesis route to enantiomerically pure jasmonoids

M Ernst, G Helmchen - Angewandte Chemie International …, 2002 - Wiley Online Library
12-Oxophytodienoic acid (12-OPDA)(1), ubiquitous in the plant kingdom, is the biosynthetic
precursor for the jasmonoids 2±7. These compounds result from 1 via the so-called …

Syntheses of methyl jasmonate and analogues

C Chapuis, D Skuy, CA Richard - Chimia, 2019 - chimia.ch
This account corresponds to the presentation given by the main author on the occasion of
the 2nd Swiss Industrial Symposium in Basel (October 19th, 2018). After a short historical …

A General Enantioselective Approach to Jasmonoid Fragrances:  Synthesis of (+)-(1R,2S)-Methyl Dihydrojasmonate and (+)-(1R,2S)-Magnolione

A Porta, G Vidari, G Zanoni - The Journal of Organic Chemistry, 2005 - ACS Publications
Methyl dihydrojasmonate 1 and magnolione 3 are of both academic and industrial interest.
In this paper, we describe a flexible, high-yielding route to diastereomerically pure (+)-cis-(1 …

Industrielle Synthese von (+)‐cis‐Methyldihydrojasmonat durch enantioselektive katalytische Hydrierung; Identifizierung des Präkatalysators [Ru ((−)‐Me‐DuPHOS)(H …

DA Dobbs, KPM Vanhessche, E Brazi… - Angewandte …, 2000 - Wiley Online Library
Prototypen neuer Familien von Präkatalysatoren und Katalysatoren,[Ru ((−)‐Me‐
DuPHOS)(H)(η6‐1, 3, 5‐cyclooctatrien)](BF4) und der daraus zugängliche Komplex „[Ru …

Route scouting towards a methyl jasmonate precursor

C Chapuis, E Walther, F Robvieux… - Helvetica Chimica …, 2016 - Wiley Online Library
For the synthesis of methyl jasmonate (1), via the strategic intermediates 3, 4, and 6a, we
constructed a synthetic network via the diverse intermediates 7–10, 13, 14, 17, and 18. This …

Methyl Homologues of Methyl Jasmonate and Methyl Dihydrojasmonate (Hedione®) from Sorbyl Alcohol

W Giersch, I Farris - Helvetica chimica acta, 2004 - Wiley Online Library
Abstract Treatment of cycloalkanone dimethyl acetals 3–6 with sorbyl alcohol (=(2E, 4E)‐
hexa‐2, 4‐dien‐1‐ol; 1) in the presence of acids afforded the novel cycloalkenones 8, 9, 11 …

Flavours and fragrances

B Schaefer, B Schaefer - Natural Products in the Chemical Industry, 2014 - Springer
Flavours and fragrances constitute some of the most beautiful and amazing facets of
chemistry. Whereas in many respects chemistry is a very purpose-oriented science …