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  • A simple and efficient highly enantioselective synthesis of alpha-ionone and alpha-damascone.

A simple and efficient highly enantioselective synthesis of alpha-ionone and alpha-damascone.

The Journal of organic chemistry (2004-12-04)
Marcella Bovolenta, Francesca Castronovo, Alessandro Vadalà, Giuseppe Zanoni, Giovanni Vidari
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.

MATERIALS
Product Number
Brand
Product Description

Supelco
α-Damascone, analytical standard
Pricing and availability is not currently available.
Sigma-Aldrich
α-Ionone, technical grade, 90%
Pricing and availability is not currently available.
Sigma-Aldrich
α-Ionone, ≥90%, stabilized
Pricing and availability is not currently available.