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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F25%3A73632488" target="_blank" >RIV/61989592:15310/25:73632488 - isvavai.cz</a>

Výsledek na webu

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500020" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500020</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ceur.202500020" target="_blank" >10.1002/ceur.202500020</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

Herein, a detailed account of the efforts leading to the recently published synthesis of the Ganoderma meroterpenoid ganoapplanin, a natural product identified as an inhibitor of T-type voltage-gated calcium channels, is provided. Ganoapplanin, which was isolated as a racemate from the fungus Ganoderma applanatum in 2016, features a complex structure, including a characteristic spiro bisacetal structure, a highly functionalized tetra-ortho-substituted biaryl motif, and a propellane-like dioxatricyclo[4.3.3.0]dodecane scaffold. While the southern terpenoid fragment is available via a diastereoselective titanium-mediated iodolactonization, considerable efforts are required to fuse this fragment with various aromatic fragments. The breakthrough was achieved by a highly efficient two-component coupling strategy that simultaneously fuses the fragments and establishes the crucial biaryl bond. This transformation involves an intramolecular 6-exo-trig radical addition of a quinone monoacetal, followed by an intermolecular aldol addition. Finally, strategic late-stage oxidations enabled the formation of the characteristic spiro bisacetal motif and the completion of the synthesis of ganoapplanin.

Název v anglickém jazyce

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

Popis výsledku anglicky

Herein, a detailed account of the efforts leading to the recently published synthesis of the Ganoderma meroterpenoid ganoapplanin, a natural product identified as an inhibitor of T-type voltage-gated calcium channels, is provided. Ganoapplanin, which was isolated as a racemate from the fungus Ganoderma applanatum in 2016, features a complex structure, including a characteristic spiro bisacetal structure, a highly functionalized tetra-ortho-substituted biaryl motif, and a propellane-like dioxatricyclo[4.3.3.0]dodecane scaffold. While the southern terpenoid fragment is available via a diastereoselective titanium-mediated iodolactonization, considerable efforts are required to fuse this fragment with various aromatic fragments. The breakthrough was achieved by a highly efficient two-component coupling strategy that simultaneously fuses the fragments and establishes the crucial biaryl bond. This transformation involves an intramolecular 6-exo-trig radical addition of a quinone monoacetal, followed by an intermolecular aldol addition. Finally, strategic late-stage oxidations enabled the formation of the characteristic spiro bisacetal motif and the completion of the synthesis of ganoapplanin.

Druh

J_ost - Ostatní články v recenzovaných periodicích

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

N - Vyzkumna aktivita podporovana z neverejnych zdroju

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ChemistryEurope

ISSN

2751-4765

e-ISSN

2751-4765

Svazek periodika

3

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

21

Strana od-do

"e202500020-1"-"e202500020-21"

Kód UT WoS článku

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EID výsledku v databázi Scopus

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