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Structure-Odor Correlation XVII. Synthesis and Olfactory Properties of further Theaspirane Analogs

✍ Scribed by Weyerstahl, Peter ;Schneider, Kathleen

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
383 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Alkylation of ethyl geranate (5) with the bromo esters 7 and 8 gave the β,γ‐unsaturated esters 10 and 11, which could be isomerized to 13 and 14 by treatment with DBU. The α,β‐unsaturated esters 12–14 were cyclized to 15–17, and subsequent reduction of 15–17 led to the diols 18–20. Final cyclization afforded the spiro ethers 2–4. – The olfactive properties (intensity and quality) of the theaspirane analogs 1–4 are determined by the conformational flexibility of the respective molecule. Thus, the rigid 1 and 2 have strong camphoraceous odors. Augmenting flexibility (→3, →4) results in weaker, fruity‐woody notes.

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