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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

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

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

Project

<a href="/en/project/LM2018110" target="_blank" >LM2018110: CzechNanoLab research infrastructure</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2023

Confidentiality

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

Name of the periodical

International Journal of Molecular Sciences

ISSN

1661-6596

e-ISSN

—

Volume of the periodical

24

Issue of the periodical within the volume

12

Country of publishing house

CH - SWITZERLAND

Number of pages

9

Pages from-to

10331

UT code for WoS article

001017405300001

EID of the result in the Scopus database

2-s2.0-85163951395