Divergent Synthesis of Natural Benzyl Salicylate and Benzyl Gentisate Glucosides

Dariya D. Fedorova, Dariya S. Nazarova, David L. Avetyan, Andrey Shatskiy, Maxim L. Belyanin, Markus D. Kärkäs, Elena V. Stepanova

Research output: Contribution to journalArticlepeer-review

Abstract

Herein is reported the first total synthesis of benzyl salicylate and benzyl gentisate glucosides present in various plant species, in particular the Salix genus, such as Populus balsamifera and P. trichocarpa. The method permits the synthesis of several natural phenolic acid derivatives and their glucosides starting from salicylic or gentisic acid. The divergent approach afforded access to three different acetylated glucosides from a common synthetic intermediate. The key step in the total synthesis of naturally occurring glycosides - the selective deacetylation of the sugar moiety - was achieved in the presence of a labile benzyl ester group by employing mild deacetylation conditions. The protocol permitted synthesis of trichocarpine (4 steps, 40% overall yield), isotrichocarpine (3 steps, 51% overall yield), trichoside (6 steps, 40% overall yield), and deoxytrichocarpine (3 steps, 42% overall yield) for the first time (>95% purity). Also, the optimized mild deacetylation conditions allowed synthesis of 2-O-acetylated derivatives of all four glycosides (5-17% overall yield, 90-95% purity), which are rare plant metabolites.

Original languageEnglish
Pages (from-to)3173-3180
Number of pages8
JournalJournal of Natural Products
Volume83
Issue number10
DOIs
Publication statusPublished - 23 Oct 2020

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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