Total Synthesis of Ganoapplanin Enabled by a Radical Addition/Aldol Reaction Cascade

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F24%3A73626666" target="_blank" >RIV/61989592:15310/24:73626666 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.acs.org/doi/epdf/10.1021/jacs.4c08291?ref=article_openPDF" target="_blank" >https://pubs.acs.org/doi/epdf/10.1021/jacs.4c08291?ref=article_openPDF</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/jacs.4c08291" target="_blank" >10.1021/jacs.4c08291</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Total Synthesis of Ganoapplanin Enabled by a Radical Addition/Aldol Reaction Cascade

Popis výsledku v původním jazyce

The total synthesis of the Ganoderma meroterpenoid ganoapplanin, an inhibitor of T-type voltage-gated calcium channels, is reported. Our synthetic approach is based on the convergent coupling of a readily available aromatic polyketide scaffold with a bicyclic terpenoid fragment. The three contiguous stereocenters of the terpenoid fragment, two of which are quaternary, were constructed by a diastereoselective, titanium-mediated iodolactonization. For the fusion of the two fragments and to simultaneously install the crucial biaryl bond, we devised a highly effective two-component coupling strategy. This event involves an intramolecular 6-exo-trig radical addition of a quinone monoacetal followed by an intermolecular aldol reaction. A strategic late-stage oxidation sequence allowed the selective installation of the remaining oxygen functionalities and the introduction of the characteristic spiro bisacetal structure of ganoapplanin

Název v anglickém jazyce

Total Synthesis of Ganoapplanin Enabled by a Radical Addition/Aldol Reaction Cascade

Popis výsledku anglicky

The total synthesis of the Ganoderma meroterpenoid ganoapplanin, an inhibitor of T-type voltage-gated calcium channels, is reported. Our synthetic approach is based on the convergent coupling of a readily available aromatic polyketide scaffold with a bicyclic terpenoid fragment. The three contiguous stereocenters of the terpenoid fragment, two of which are quaternary, were constructed by a diastereoselective, titanium-mediated iodolactonization. For the fusion of the two fragments and to simultaneously install the crucial biaryl bond, we devised a highly effective two-component coupling strategy. This event involves an intramolecular 6-exo-trig radical addition of a quinone monoacetal followed by an intermolecular aldol reaction. A strategic late-stage oxidation sequence allowed the selective installation of the remaining oxygen functionalities and the introduction of the characteristic spiro bisacetal structure of ganoapplanin

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

N - Vyzkumna aktivita podporovana z neverejnych zdroju

Rok uplatnění

2024

Kód důvěrnosti údajů

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

Název periodika

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

ISSN

0002-7863

e-ISSN

1520-5126

Svazek periodika

146

Číslo periodika v rámci svazku

33

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

22937-22942

Kód UT WoS článku

001286271500001

EID výsledku v databázi Scopus

2-s2.0-85200806113