New terpenyl sulfides of the pinane series have been synthesized from (-)-b-pinene, cis-and trans-verbenols, and myrtenol. Screening for antifungal activity of the monoterpenoids of the pinane series has been carried out. The relationship between the structure and antifungal properties of the synthesized compounds has been established.

Attachment of 2-mercaptoethanol and thioglycolic acid methyl ester to the double bond of (1S)-(-)-b-pinene yielded pinane sulfides with the cis configuration. Oxidation of sulfides with m-chloroperbenzoic acid yielded the corresponding sulfoxides and sulfones. The resulting compounds were screened for antimycotic activity and the dynamics of changes in antifungal properties in sulfides-sulfoxide-sulfone series were studied.

A total of 33 compounds including bicyclic monoterpenes, oxides, allyl alcohols, and S-containing pinane and carane derivatives were screened for antifungal activity against mycelial and yeast-like fungi. The structure-activity relationship was studied. The most active antimycotics were found.Keywords: carane and pinane monoterpenoids, antifungal activity.We performed for the first time a systematic study of the antifungal activity of series of pinane and carane monoterpenoids with a broad set of S-containing functional groups and studied the structure-activity relationship to find the most active antimycotics.At the start of our work, the literature contained data on the antifungal activity of D-and E-pinenes in addition to the antifungal effect of essential oils containing (+)-3-carene (1), verbenols, and myrtenol [1][2][3][4][5]. However, the antifungal activity of S-containing terpenoids was not previously investigated.Carane thioterpenoids 4-15 were synthesized by reacting stereoisomeric 3-carene oxides (2 and 3) with thiols (4, 5, 10, 11, 15), isothiuronium salts (6-9, 13, 14), and thiourea (16) in the presence of sodium ethoxide [6-9]. Sulfoxide 12 was obtained by oxidation of 6 with H 2 O 2 in glacial acetic acid. The products were isolated by column chromatography. The structures were established using spectral data.

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