Unexpectedly Regioselective Diels-Alder Reactions of New Unsymmetrical Benzoquinones: A Convenient Synthetic Entry to Uniquely Substituted Decalins
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68081707%3A_____%2F24%3A00599429" target="_blank" >RIV/68081707:_____/24:00599429 - isvavai.cz</a>
Alternative codes found
RIV/00159816:_____/24:00081416 RIV/00216224:14310/24:00137337
Result on the web
<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202401068" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202401068</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.202401068" target="_blank" >10.1002/chem.202401068</a>
Alternative languages
Result language
angličtina
Original language name
Unexpectedly Regioselective Diels-Alder Reactions of New Unsymmetrical Benzoquinones: A Convenient Synthetic Entry to Uniquely Substituted Decalins
Original language description
We report flexible synthesis of new unsymmetrically 2,6-disubstituted benzoquinones (33 examples) and a systematic study of their reactivity in the Diels-Alder reaction. The Diels-Alder reactions of selected unsymmetrical benzoquinones with seemingly similar substituents were found to proceed with high regioselectivity and the formation of selected experimentally observed main products was rationalized by theoretical (DFT) calculations. The findings can be exploited in the convenient preparation of densely substituted and stereochemically defined decalins with unique angular substituents at ring fusion. We also demonstrate the usefulness of this methodology in complex molecule synthesis through the total synthesis of a novel forskolin analog possessing an ethyl group at the fusion of the rings B and C.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - 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
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
1521-3765
Volume of the periodical
30
Issue of the periodical within the volume
55
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
e202401068
UT code for WoS article
001327935200015
EID of the result in the Scopus database
2-s2.0-85205524616