| Autor: |
Dr. Khoa Linh Pham, Prof. Dr. Martin E. Maier |
| Jazyk: |
angličtina |
| Rok vydání: |
2024 |
| Předmět: |
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| Zdroj: |
ChemistryOpen, Vol 13, Iss 10, Pp n/a-n/a (2024) |
| Druh dokumentu: |
article |
| ISSN: |
2191-1363 |
| DOI: |
10.1002/open.202400103 |
| Popis: |
Abstract Among the natural tetramic acids with a decalinoyl part, signermycin B is unique because it contains a cis‐decalin. In this paper, we demonstrate that the cis‐decalin section of signermycin B can be accessed by an anionic oxy‐Cope rearrangement. The substrate, a tricyclic dienol was prepared by an intramolecular Diels‐Alder reaction of a masked ortho‐benzoquinone, generated by oxidation of an α‐methoxyphenol in presence of cis‐2‐hexenol. After a superfluous bromine on the cycloadduct was removed, reaction of the tricyclic ketone with isopropenylmagnesium bromide led to the tricyclic trienol that underwent the oxy‐Cope rearrangement to a cis‐decalinone. While we could show, that introduction of the 4‐ethyl substituent (signermycin B numbering) is possible by enolate alkylation, the 4‐epi‐isomer was formed. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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