A General Entry to Ganoderma Meroterpenoids: Synthesis of Applanatumol E, H, and I, Lingzhilactone B, Meroapplanin B, and Lingzhiol

2024/10/11 by Alexander Rode, Nicolas Müller, Ondřej Kováč +2 · 1 voice · 1 citation
Agricultural and Biological Sciences · Medicine · Pharmacology, Toxicology and Pharmaceutics · #Fungal Biology and Applications #Phytochemistry and Bioactivity Studies #Polysaccharides and Plant Cell Walls

paper · pdf · doi:10.1021/acs.orglett.4c03192

openalex publication_date 2024/10/11 · openalex created_date 2024/10/12 · openalex updated_date 2026/08/01

Abstract

meroterpenoids are fungal derived hybrid natural product class containing a 1,2,4-trisubstituted benzene ring and a polycyclic terpenoid part. The representatives applanatumol E, H and I, lingzhilactone B, and meroapplanin B share the same bicyclic lactone moiety connected to the arene. Employing photo-Fries rearrangements as the key step enabled a general entry to these natural products. For the synthesis of the tetracyclic framework of lingzhiol, we made use of a powerful photoredox oxidative decarboxylation/Friedel-Crafts sequence.

Cited by

• Evolution of a Strategy for the Total Synthesis of the Ganoderma Meroterpenoid Ganoapplanin

Discussions

• The natural product is lingzhiol, and we studied Magauer's recent manuscript, which included the synthesis of five other Ganoderma meroterpenoids: doi.org/10.1021/acs.orglett.4c03192 [bsky, 2 points, 0 comments]

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