ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
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Benzylic functionalization of dehydroabietane derivatives as a convenient way to sulfur compounds

Evgeniy S. Izmest’ev, Svetlana V. Pestova, Dmitriy V. Petukhov, and Svetlana A. Rubtsova

Institute of Chemistry, Federal Research Center “Komi Science Center of the Ural Branch of the Russian Academy of Sciences”, Syktyvkar, Russian Federation

 

E-mail: evgeniyizmestev@rambler.ru

Received: 25 February 2022  Accepted: 13 April 2022

Abstract:

For the first time, dehydroabietane-derived alcohols containing an OH group at the C-7 position were used to produce thioacetates by direct ZnCl2-catalyzed substitution of the hydroxyl group. Thioacetates obtained were found to give the corresponding disulfides when treated with MeONa in the presence of atmospheric oxygen with no observation of any thiol formation. In addition, the ability of diol with two hydroxyl groups at C-7 and C-18 to be converted to a cyclic dimer was detected. Dehydroabietane derivatives with a sulfur atom at the C-7 position (thiol, disulfides), which are promising for the production of biologically active substances, were first obtained.

Graphical abstract

Keywords: Diterpenoids; Dehydroabietane; Thiols; Thioacetates; Disulfides

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02234-9

 

Chemical Papers 76 (8) 5033–5042 (2022)

Wednesday, July 24, 2024

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