Cross-Coupling as a Key Step in the Synthesis and Structure Revision of the Natural Products Selagibenzophenones A and B

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F21%3A10430706" target="_blank" >RIV/00216208:11310/21:10430706 - isvavai.cz</a>

Result on the web

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=6BwmO_lxqi" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=6BwmO_lxqi</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/catal11060708" target="_blank" >10.3390/catal11060708</a>

Result language

angličtina

Original language name

Cross-Coupling as a Key Step in the Synthesis and Structure Revision of the Natural Products Selagibenzophenones A and B

Original language description

Selagibenzophenone A (1) and its isomer selagibenzophenone B (2) were recently described as natural products from Selaginella genus plants with PDE4 inhibitory activity. Herein, we report the first total syntheses of both compounds. By comparing spectroscopic data of the synthetic compounds with reported data for the isolated material, we demonstrate that the structure of one of the two natural products was incorrectly assigned, and that in fact isolated selagibenzophenone A and selagibenzophenone B are identical compounds. The synthetic strategy for both 1 and 2 is based on a cross-coupling reaction and on the addition of organometallic species to assemble the framework of the molecules. Identifying a suitable starting material with the correct substitution pattern is crucial because its pattern is reflected in that of the targeted compounds. These syntheses are finalized via global deprotection. Protecting the phenols as methoxy groups provides the possibility for partial control over the selectivity in the demethylation thanks to differences in the reactivity of the various methoxy groups. Our findings may help in future syntheses of derivatives of the biologically active natural product and in understanding the structure-activity relationship.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2021

Confidentiality

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

Name of the periodical

Catalysts [online]

ISSN

2073-4344

e-ISSN

—

Volume of the periodical

11

Issue of the periodical within the volume

6

Country of publishing house

CH - SWITZERLAND

Number of pages

13

Pages from-to

708

UT code for WoS article

000665419300001

EID of the result in the Scopus database

2-s2.0-85107187722