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Terpenoids Derived from Linalyl Oxide. Part 3. The isolation, structure, absolute configuration and synthesis of the davanafurans, nor-sesquiterpenes isolated from Artemisia Pallens

✍ Scribed by Alan F. Thomas; Renée Dubini

Publisher: John Wiley and Sons
Year: 1974
Tongue: German
Weight: 589 KB
Volume: 57
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19740570718

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✦ Synopsis

Abstract

The novel nor‐sesquiterpenoids, the davanafurans, have been isolated from the oil of Artemisia pallens, the principal component being the cis, threo‐isomer (1a). The absolute configuration of this isomer, and the relative stereochemistry of the other isomers, have been established by synthesis from linalool oxides of known configuration.

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## Abstract The isolation, absolute stereochemistry, and synthesis of a new C~11~‐terpenoid, 3__S__,4__S__,7__R__‐3,7‐dimethyl‐4,7‐oxido‐non‐8‐en‐2‐one, related to davanone, are described.

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Terpenoids Derived from Linalyl Oxide, Part 4. The oxidation of davanone. Isolation and synthesis of the davana ethers, sesquiterpenes of Artemisia Pallens

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## Abstract The photosensitized oxygenation of the β,γ‐unsaturated ketonic sesquiterpene, davanone, is described. Treatment of davanone epoxide with an acid ion exchange resin yields a stereoisomeric mixture of the davana ethers, sesquiterpenoids containing two reduced furan rings.