Oxidative Cleavage and Ring Reconstruction for the Synthesis of Amaryllidaceae Alkaloid Analogues

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F24%3A10478574" target="_blank" >RIV/00216208:11310/24:10478574 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=yY6s1wlfiX" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=yY6s1wlfiX</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.202301021" target="_blank" >10.1002/ejoc.202301021</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Oxidative Cleavage and Ring Reconstruction for the Synthesis of Amaryllidaceae Alkaloid Analogues

Popis výsledku v původním jazyce

This study presents the synthesis of analogues of bioactive Amaryllidaceae alkaloids that contain a five-membered ring C and a quaternary carbon centre. The synthesis was carried out in a divergent manner, starting from a common intermediate, keto aldehyde 1 a. This intermediate was obtained by oxidative cleavage of a carbocyclic ring present in the previously synthesised tetracyclic compounds. Subsequent closure of a new heterocyclic ring B using different methods led to products with structural cores found in naturally occurring alkaloids such as pretazettine, tazettine or macronine. In addition, an analogue of egonine was prepared from the same intermediate. Our approach thus provides access to multiple structural types of potentially bioactive molecules.

Název v anglickém jazyce

Oxidative Cleavage and Ring Reconstruction for the Synthesis of Amaryllidaceae Alkaloid Analogues

Popis výsledku anglicky

This study presents the synthesis of analogues of bioactive Amaryllidaceae alkaloids that contain a five-membered ring C and a quaternary carbon centre. The synthesis was carried out in a divergent manner, starting from a common intermediate, keto aldehyde 1 a. This intermediate was obtained by oxidative cleavage of a carbocyclic ring present in the previously synthesised tetracyclic compounds. Subsequent closure of a new heterocyclic ring B using different methods led to products with structural cores found in naturally occurring alkaloids such as pretazettine, tazettine or macronine. In addition, an analogue of egonine was prepared from the same intermediate. Our approach thus provides access to multiple structural types of potentially bioactive molecules.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

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

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

1099-0690

Svazek periodika

27

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

7

Strana od-do

e202301021

Kód UT WoS článku

001119807500001

EID výsledku v databázi Scopus

2-s2.0-85179302689