ArticleAngewandte Chemie (International ed. in English)2021
Concise Total Synthesis of Agarozizanol B via a Strained Photocascade Intermediate.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Dearomatization of Aromatic Carbonyl Compounds by Photocycloaddition Reactions to 1,1-Dimethylallene.Organic letters · 2026Article
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- IntramolecularThe Journal of organic chemistry · 2025Article
- Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds.Beilstein journal of organic chemistry · 2025Review
- Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate.Chemical communications (Cambridge, England) · 2023Article
- UV light-driven late-stage skeletal reorganization to diverse limonoid frameworks: A proof of concept for photobiosynthesis.Science advances · 2023Article
- Arene Activation through Iminium Ions: Product Diversity from Intramolecular Photocycloaddition Reactions.Angewandte Chemie (International ed. in English) · 2022Article
- Total syntheses of strained polycyclic terpenes.Chemical communications (Cambridge, England) · 2022Review
- Concise Total Synthesis of Agarozizanol B via a Strained Photocascade Intermediate.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
4 authors.
Funding
Abstract
The prezizane-type sesquiterpene agarozizanol B was synthesized employing a photochemical cascade reaction as the key step. Starting from a readily available 1-indanone with a tethered olefin, a strained tetracyclic skeleton was assembled which contained all carbon atoms of the sesquiterpene with the correct relative configuration. The conversion into the tricyclic prezizane skeleton was accomplished by a strategic cyclopropane bond cleavage. Prior to the cyclopropane ring opening an adaption of the oxidation state was required, which could be combined with a reductive resolution step. After removal of two functional groups, the natural product was obtained both in racemic form or, if resolved, as the (+)-enantiomer which was shown to be identical to the natural product.
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