79-68-5Relevant articles and documents
Enzyme-mediated syntheses of the enantiomers of γ-irones
Brenna, Elisabetta,Fuganti, Claudio,Ronzani, Sabrina,Serra, Stefano
, p. 3650 - 3666 (2007/10/03)
An enzymatic approach to the synthesis of all the possible stereoisomers of (E) and (Z), cis and trans-γ-irones in enantiomerically pure form from commercial Irone Alpha is described. A very efficient resolution of racemic trans-γ-irone, affording both the enantiomers in high ee and chemical purity, is also presented. Olfactory evaluation of (+)- and (-)-3b and full configuration assignment of the irone isomers contained in samples of Italian iris oil are reported.
Synthesis of (+)-(2S,6S)-trans-α-Irone and of (-)-(2S,6S)-trans-γ-Irone
Helmlinger, Daniel,Frater, Georg
, p. 1515 - 1521 (2007/10/02)
A 3:1 mixture of (+)-(2S,6S)-trans-α-irone ((+)-1) and (-)-(2S,6S)-trans-γ-irone ((-)-2) has been synthesized with ca. 70 percent e. e. by the ene reaction of (-)-(S)-3 and but-3-yn-2-one.
CHIMIE DES FRAGRANCES, PARTIE II: SYNTHESE DE LA γ-IONONE ET DES CIS- ET TRANS-γ-IRONES
Leyendecker, Francois,Comte, Marie-Therese
, p. 85 - 92 (2007/10/02)
A new convergent synthesis of γ-ionone and cis- and trans-γ-irones is described.A tandem 1,4-addition functionnalisation reaction and a chemo- and regioselective olefination reaction are the key steps.A two dimensional NMR study allows the determination of the favoured configuration of one intermediate.