ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A-F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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6 citing papers in PubMed, 14 citations in OpenAlex.
- Cobalt catalysis in organic synthesis: a powerful tool in the synthesis of natural products and pharmaceutically active compounds.RSC advances · 2026Review
- Pseudopterosin Biosynthesis: Unravelling a Decades Old Problem in Animal Specialized Metabolism.Journal of the American Chemical Society · 2025Article
- Autoxidation of a C2-Olefinated Dihydroartemisinic Acid Analogue to Form an Aromatic Ring: Application to Serrulatene Biosynthesis.Journal of natural products · 2022Review
- Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis.Frontiers in chemistry · 2022Review
- Understanding the competing pathways leading to hydropyrene and isoelisabethatriene.Beilstein journal of organic chemistry · 2022Article
- Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A-F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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9 authors at 1 institution in 1 country.
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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.
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