Concise Total Synthesis of Agarozizanol B via a Strained Photocascade Intermediate
| Autor: | Line Næsborg, Thorsten Bach, Niklas Rauscher, Christian Jandl |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Olefin fiber
photochemistry Stereochemistry Communication domino reactions Total synthesis General Medicine General Chemistry diastereoselectivity Ring (chemistry) Communications Catalysis Cycloaddition Cyclopropane chemistry.chemical_compound chemistry Cascade reaction Total Synthesis | Very Important Paper terpenoids Oxidation state total synthesis cycloaddition Bond cleavage |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.202110009 |
| Popis: | 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. Starting from a simple indanone derivative, diastereomerically pure intermediate 1 was formed in a photochemical cascade and served as precursor to agarozizanol B (2), either as racemate or as single enantiomer after a resolution step. |
| Databáze: | OpenAIRE |
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