Formal Total Synthesis of Salvinorin A
Abstract: The generation of the quaternary stereocenter at the C9 position of salvinorin A precursors by the Claisen rearrangement was investigated. The required allyl alcohol was prepared from a Wieland‐Miescher ketone using a known γ‐hydroxylation, reduction of the enone double bond, cyanohydrin formation, and elimination, yielding an unsaturated nitrile. A two‐step reduction led to the required allyl alcohol. The subsequent Johnson‐Claisen rearrangement provided a mixture of two diastereomeric 1,4‐unsaturated esters in a ratio of around 2.6: 1. The major isomer could be converted to a key intermediate of the Hagiwara synthesis of salvinorin A.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Formal Total Synthesis of Salvinorin A ; day:26 ; month:02 ; year:2022 ; extent:1
ChemistryOpen ; (26.02.2022) (gesamt 1)
- Creator
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Halang, Marc
Maier, Martin E.
- DOI
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10.1002/open.202200015
- URN
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urn:nbn:de:101:1-2022022614104539016962
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:23 AM CEST
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Associated
- Halang, Marc
- Maier, Martin E.
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