Bioactives terpenoids. Synthesis of oxygenated derivatives of cariolan-1-ol starting from caryophyllene.

MURO ANA CAROLINA; GULTEMIRIAN MARÍA DE LOURDES; VILLECO M. B.; CATALÁN C. A. N.

BIOCELL

INST HISTOL EMBRIOL-CONICET

Año: 2003 vol. 27 p. 122 - 122

0327-9545

The sesquiterpene hydrocarbon caryophillene (1) and its oxygenated derivatives are widely distributed in the plant kingdom. Caryophillene itself has aphid repellent and antifeedant activity. The unusual structure of 1 provides the basis for a variety of transformations leading to tricyclic sesquiterpenoids with stronger bioactivity than the parent compound. We report here the synthesis of oxygenated derivatives of cariolan-1-ol (2), a tricyclic sesquiterpene tertiary alcohol easily obtained by acid hydratation of 1. Chromyl acetate oxidation of 2 proceeded with a relatively high regioselectivity to give a mixture of three cetoalchols (44.6, 21.1 and 2.9%), one diketoalcohol (5.8%) and three hydroxyacetates (13.6, 10.7 and 1.2%). The main oxidation product resulted to be 6-oxo-cariolan-1-ol. After isolation the compounds will be used to test their antibacterial, antifungal and antifeedant activities as well as their value as flavoring substances