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Total Synthesis of (+)‐Erogorgiaene and the Pseudopterosin A−F Aglycone via Enantioselective Cobalt‐Catalyzed Hydrovinylation

  • Abstract Due to their pronounced bioactivity and limited availability from natural resources, metabolites of the soft coral Pseudopterogorgia elisabethae, such as erogorgiaene and the pseudopterosines, represent important target molecules for chemical synthesis. We have now developed a particularly short and efficient route towards these marine diterpenes exploiting an operationally convenient enantioselective cobalt‐catalyzed hydrovinylation as the chirogenic step. Other noteworthy C−C bond forming transformations include diastereoselective Lewis acid‐mediated cyclizations, a Suzuki coupling and a carbonyl ene reaction. Starting from 4‐methyl‐styrene the anti‐tubercular agent (+)‐erogorgiaene (>98 % ee) was prepared in only 7 steps with 46 % overall yield. In addition, the synthesis of the pseudopterosin A aglycone was achieved in 12 steps with 30 % overall yield and, surprisingly, was found to exhibit a similar anti‐inflammatory activity (inhibition of LPS‐induced NF‐κB activation) as a natural mixture of pseudopterosins A−D or iso‐pseudopterosin A, prepared by β‐D‐xylosylation of the synthetic aglycone.
Metadaten
Verfasserangaben:Sohajl Movahhed, Julia Westphal, Alexander Kempa, Christian Eric Schumacher, Julia Sperlich, Jörg‐Martin Neudörfl, Nicole Teusch, Matthias Hochgürtel, Hans‐Günther Schmalz
URN:urn:nbn:de:hbz:832-epub4-19557
DOI:https://doi.org/10.1002/chem.202101863
Titel des übergeordneten Werkes (Englisch):Chemistry – A European Journal
Dokumentart:Wissenschaftlicher Artikel
Sprache:Englisch
Datum der Veröffentlichung:13.08.2021
Datum der Freigabe:06.04.2022
GND-Schlagwort:Diterpene; Glykoside
Freies Schlagwort / Tag:Cationic Cyclization; Cobalt Catalysis; Diterpenes; Glycosides; Hydrovinylation; Marine Natural Products
Jahrgang:27
Ausgabe / Heft:45
Seitenzahl:6
Fakultäten und Zentrale Einrichtungen:Angewandte Naturwissenschaften (F11)
DDC-Sachgruppen:600 Technik, Medizin, angewandte Wissenschaften
Lizenz (Deutsch):License LogoCreative Commons - CC BY - Namensnennung 4.0 International