Unified Total Synthesis of Diverse Meroterpenoids from Ganoderma Applanatum

0559131 - ÚOCHB 2023 RIV US eng J - Článek v odborném periodiku
Šimek, Michal - Bártová, Kateřina - Issad, Samy - Hájek, Miroslav - Císařová, I. - Jahn, Ullrich
Unified Total Synthesis of Diverse Meroterpenoids from Ganoderma Applanatum.
Organic Letters. Roč. 24, č. 25 (2022), s. 4552-4556. ISSN 1523-7060. E-ISSN 1523-7052
Grant CEP: GA ČR(CZ) GA16-18513S
Institucionální podpora: RVO:61388963
Klíčová slova: mild * debenzylation * aldehydes
Obor OECD: Organic chemistry
Impakt faktor: 5.2, rok: 2022
Způsob publikování: Omezený přístup
https://doi.org/10.1021/acs.orglett.2c01633

A unified approach to meroterpenoids applanatumols B, V, W, X, and Y produced by the medicinal fungus Ganoderma applanatum and 2′-epi-spiroapplanatumine O is presented. The key synthetic sequence consists of a tandem anionic ketone allylation/oxy-Cope rearrangement/α-oxygenation furnishing an α-aminoxy ketone and a persistent radical effect-based 5-exo-trig cyclization leading to the trisubstituted cyclopentane core. The relative configuration of applanatumol V has to be revised. Some compounds display significant cytotoxic and antioxidant properties.
Trvalý link: https://hdl.handle.net/11104/0332550


Vědecká data: CCDC, CCDC, CCDC, CCDC, CCDC