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Synthesis of Novel Chiral 18‐Sulfanyl and Sulfonyl Dehydroabietane Derivatives
Author(s) -
Izmest'ev Yevgeniy S.,
Pestova Svetlana V.,
Lezina Ol'ga M.,
Rubtsova Svetlana A.,
Kutchin Aleksandr V.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902600
Subject(s) - chemistry , sulfonyl , sulfanyl , pharmacophore , sulfonic acid , alkyl , aryl , organic chemistry , chlorine , monosaccharide , disulfide bond , catalysis , combinatorial chemistry , stereochemistry , biochemistry
For the first time, dehydroabietic acid ethyl ester was used as initial material to produce the corresponding at the C‐18 position thioacetate, thiol, disulfide, sulfonic acid and sulfonyl chloride which open up prospects for the synthesis of other polyfunctional compounds combining a biologically active dehydroabietane fragment with various pharmacophore groups. The optimal conditions were found to directly oxidize dehydroabietanthiol to sulfochloride using chlorine dioxide as an oxidant in the presence of vanadyl acetylacetonate as a catalyst. This sulfochloride synthesized was proposed to use for obtaining a series of sulfonamides with alkyl, aryl, hetaryl and monosaccharide fragments.