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A Simple and Efficient Highly Enantioselective Synthesis of Alpha-Ionone and Alpha-Damascone

Marcella Bovolenta, Francesca Castronovo, Alessandro Vadalà, Giuseppe Zanoni, Giovanni Vidari

J Org Chem. 2004 Dec 10;69(25):8959-62.

PMID: 15575784

Abstract:

An efficient highly enantioselective (ee > or =99%) synthesis of alpha-ionone and alpha-damascone is described. Both enantiomers of title compounds were synthesized through two straightforward pathways diverging from enantiopure (R)- or (S)-alpha-cyclogeraniol. These versatile building blocks were obtained by regioselective ZrCl(4)-promoted biomimetic cyclization of (6S)- or (6R)-(Z)-6,7-epoxygeraniol, respectively, followed by deoxygenation of the so formed secondary alcohol. The chiral information was encoded by a highly regioselecive Sharpless asymmetric dihydroxylation of inexpensive geranyl acetate.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP43052875 Alpha-Damascone Alpha-Damascone 43052-87-5 Price
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