Studies Concerned with the Structure and Synthesis of the Anti-viral Tropolone Glycoside Liriosmaside A.

ABSTRACT: A bromotropone corresponding to the agylcone of the glycosylated sesquiterpenoid natural product liriosmaside A has been prepared over ten steps and in a fully regio-controlled manner through the gem-dibromocyclopropane-mediated ring-expansion of a readily accessible decalenone. A Pd[0]-mediated glucosylation reaction applied to this bromotropone afforded a product mixture from which an enantiomerically pure cross-coupling product could be obtained and its structure confirmed through single-crystal X-ray analysis of a derivative. Various (unsuccessful) attempts are described to selectively acylate the last compound and thereby install the 3-hydroxy-3-methylglutaric acid or HMGA-containing side chain of the title natural product. A literature survey of other natural products embodying the H

SUBMITTER: Chen Q 

PROVIDER: S-EPMC12368893 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature