Authors
Marvin Wenninger, Maxim Munt, Le Chang, Rositsa Stoykova, Roberto Ojcius, Oliver Spieß, Dieter Schinzer
Published in
Chemistry (Weinheim an der Bergstrasse, Germany). Pages e71360. Jul 02, 2026. Epub Jul 02, 2026.
Abstract
Herein, we report the synthesis of the three key fragments of the macrolide antibiotic (+)-neosorangicin A, a compound exhibiting potent activity against multiple pathogens. The tetrahydropyran unit (THP) was prepared via stereocontrolled Brown crotylation, followed by hydroboration and epoxide-opening/cyclization steps. Subsequent coupling with the known dioxabicyclo[3.2.1]octane fragment (BCO) via Grubbs metathesis furnished the THP-BCO key intermediate on a gram scale. This intermediate was further transformed into an E-vinyl iodide for a late-stage Stille coupling with the dihydropyran fragment (DHP), incorporating a shortened side chain relative to (+)-sorangicin A and bearing a secondary alcohol. This fragment was synthesized via 1,2-addition to a dihydropyran-methyl ketone followed by dehydration. Subsequent functional group manipulations enabled access to a phosphonate intermediate, which was converted into a stannylated Z,Z-diene via Ando olefination. The Stille coupling between the THP-BCO and the DHP fragments provided the carbon skeleton of the natural product and was confirmed by a relay approach using isolated (+)-neosorangicin A. This work establishes a selective route to the key building blocks, providing a foundation for the convergent total synthesis of (+)-neosorangicin A and a proof of concept via a relay approach.
PMID:
42390837
Bibliographic data and abstract were imported from PubMed on 02 Jul 2026.
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