Synthetic approaches to ring-and side-chain hydroxy derivatives of the 2-ethyl-8-methyl-1,7-dioxaspiro-[ S Slundecane system 8 are described. Alkylation reactions of diethyl3-oxopentanedioate, pentane-2,4-dione and acetone N,N-dimethylhydrazone have been employed. Appropriate choices of enantiomeric iodides in the alkylation sequences, sometimes followed by asymmetric dihydroxylation of derived hydroxyenones, have permitted access to key enantiomers of these alcohols, which have been fully characterised by 'H and 3C NMR spectroscopy, gas chromatographic-mass spectrometric methods, and chiral gas chromatography.In previous publications 1-3 we have described the synthesis of a range of spiroacetals, many of which were components of insect secretions and emissions, particularly from Australasian fruit-16 17 902

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