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Synthesis, Olfactory Evaluation, and Determination of the Absolute Configuration of the 3,4-Didehydroionone Stereoisomers by Stefano Serra; Claudio Fuganti; Elisabetta Brenna is a Chemistry article available to read on EtoBox.

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## Abstract The synthesis of 3,4‐didehydroionone isomers **4**, (+)‐**6**, and (−)‐**6** and of 3,4‐didehydro‐7,8‐dihydroionone isomers **5**, (+)‐**7**, and (−)‐**7** was accomplished starting from commercially available racemic __α__‐ionone (**1**). Their preparation of the racemic forms **4**–**7** was first achieved by mean of a number of chemo‐ and regioselective reactions (__Schemes 1__ and __2__). The enantio‐ and diastereoselective lipase‐mediated kinetic acetylation of 4‐hydroxy‐__γ__‐ionone (**10a**/**10b**) provided 4‐hydroxy‐__γ__‐ionone (+)‐**10a**/(±)‐**10b** and (+)‐4‐(acetyloxy)‐__γ__‐ionone ((+)**12b**) (__Scheme 3__). The latter compounds were used as starting materials to prepare the 3,4‐didehydro‐__γ__‐ionones (+)‐ and (−)‐**6** and the 3,4‐didehydro‐7,8‐dihydro‐__γ__‐ionones (+)‐ and (−)‐**7** in enantiomer‐enriched form. The absolute configuration of (+)‐**12b** was determine by chemical correlation with (+)‐(6__S__)‐__γ__‐ionone ((+)‐**3**) and with (−)‐(6__S__)‐__α__‐ionone ((−)‐**1**) therefore allowing to assign the (__S__)‐configuration to (+)‐**6** and (+)‐**7**. Olfactory evaluation of the above described 3,4‐didehydroionone isomers shows a significant

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Author

Stefano Serra; Claudio Fuganti; Elisabetta Brenna

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

2006

Language

EN

Field

Chemistry (Physical Sciences)