Synthetic study of natural metabolites containing a benzo[c]oxepine skeleton: heterocornol C and D

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F23%3A00573651" target="_blank" >RIV/68378271:_____/23:00573651 - isvavai.cz</a>

Výsledek na webu

<a href="https://hdl.handle.net/11104/0344050" target="_blank" >https://hdl.handle.net/11104/0344050</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/ijms241210331" target="_blank" >10.3390/ijms241210331</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthetic study of natural metabolites containing a benzo[c]oxepine skeleton: heterocornol C and D

Popis výsledku v původním jazyce

A versatile strategy for the enantioselective synthesis of a benzo[c]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki–Miyaura cross-coupling reaction for the installation of the double bond and Katsuki–Sharpless asymmetric epoxidation for the introduction of chiral centers. The first total synthesis and absolute configuration assignment of heterocornol D (3a) were achieved. Four stereoisomers, 3a, ent-3a, 3b and ent-3b, of this natural po lyketide were prepared, starting with 2,6-dihydroxy benzoic acid and divinyl carbinol. The absolute and relative configuration of heterocornol D was assigned via single-crystal X-ray analysis. The extension of the described synthetic approach is further presented with the synthesis of heterocornol C by applying the ether group reduction method to the lactone.

Název v anglickém jazyce

Synthetic study of natural metabolites containing a benzo[c]oxepine skeleton: heterocornol C and D

Popis výsledku anglicky

A versatile strategy for the enantioselective synthesis of a benzo[c]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki–Miyaura cross-coupling reaction for the installation of the double bond and Katsuki–Sharpless asymmetric epoxidation for the introduction of chiral centers. The first total synthesis and absolute configuration assignment of heterocornol D (3a) were achieved. Four stereoisomers, 3a, ent-3a, 3b and ent-3b, of this natural po lyketide were prepared, starting with 2,6-dihydroxy benzoic acid and divinyl carbinol. The absolute and relative configuration of heterocornol D was assigned via single-crystal X-ray analysis. The extension of the described synthetic approach is further presented with the synthesis of heterocornol C by applying the ether group reduction method to the lactone.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10302 - Condensed matter physics (including formerly solid state physics, supercond.)

Projekt

<a href="/cs/project/LM2018110" target="_blank" >LM2018110: Výzkumná infrastruktura CzechNanoLab</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

International Journal of Molecular Sciences

ISSN

1661-6596

e-ISSN

—

Svazek periodika

24

Číslo periodika v rámci svazku

12

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

9

Strana od-do

10331

Kód UT WoS článku

001017405300001

EID výsledku v databázi Scopus

2-s2.0-85163951395