Oxidative transformations of alkyl caryophyllanyl sulfides


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Abstract

Sesquiterpene sulfoxides and sulfones were synthesized in up to 56 and 74% yields, respectively. The oxidation of sulfides was accompanied by rearrangement of the epoxide fragment to allylic alcohol with subsequent oxidation. The isomerization of 4,5-epoxycaryophyllane-15-thiol afforded for the first time 4,11,11-trimethyl-8-(sulfanylmethyl)bicyclo[7.2.0]undec-3-en-5-ol in 40–45% yield.

About the authors

Yu. V. Gyrdymova

Institute of Chemistry, Komi Scientific Center, Ural Branch

Author for correspondence.
Email: gyrdymova-jw@chemi.komisc.ru
Russian Federation, ul. Pervomaiskaya 48, Syktyvkar, 167000

D. V. Sudarikov

Institute of Chemistry, Komi Scientific Center, Ural Branch

Email: gyrdymova-jw@chemi.komisc.ru
Russian Federation, ul. Pervomaiskaya 48, Syktyvkar, 167000

S. A. Rubtsova

Institute of Chemistry, Komi Scientific Center, Ural Branch

Email: gyrdymova-jw@chemi.komisc.ru
Russian Federation, ul. Pervomaiskaya 48, Syktyvkar, 167000

A. V. Kutchin

Institute of Chemistry, Komi Scientific Center, Ural Branch

Email: gyrdymova-jw@chemi.komisc.ru
Russian Federation, ul. Pervomaiskaya 48, Syktyvkar, 167000

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