Four stereoisomers of (þ)-pteroenone, a defensive metabolite of the abducted Antarctic pteropod Clione antarctica, were synthesized by employing anti-/syn-selective aldol reactions as the key step. These compounds displayed no antifeedant activity against a generally benthic Antarctic fish that does not cooccur with this pteropod.
Analogs of aliphatic monoterpene dienols (geraniol, nerol, linalool, and lavandulol) and non-branched alcohols (norleaf alcohol, matsutake alcohol, etc.) bearing a cyclopropane ring were synthesized, and their odor characteristics were examined. Most of the analogs show odor properties different from their parent compounds.
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