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Unexpectedly Regioselective Diels-Alder Reactions of New Unsymmetrical Benzoquinones: A Convenient Synthetic Entry to Uniquely Substituted Decalins

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MAIER Lukáš NĚMEČKOVÁ Dana AKAVARAM Naresh KALLA Erik SEMRÁD Hugo MATYASKOVÁ Olivie MUNZAROVÁ Markéta DAĎOVÁ Petra KUBALA Lukáš ŠVENDA Jakub PARUCH Kamil

Rok publikování 2024
Druh Článek v odborném periodiku
Časopis / Zdroj Chemistry - A European Journal
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
www https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202401068
Doi http://dx.doi.org/10.1002/chem.202401068
Klíčová slova Benzoquinones; Diels-Alder reaction; Decalins; Regioselectivity; Forskolin analogs
Popis 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.
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