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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

✍ Scribed by Alan F. Thomas; Renée Dubini

Publisher: John Wiley and Sons
Year: 1974
Tongue: German
Weight: 375 KB
Volume: 57
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19740570719

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

Terpenoids Derived from Linalyl Oxide. P

Terpenoids Derived from Linalyl Oxide. Part 2. The isolation and synthesis of nordavanone, A C11-terpenoid from Artemisia pallens

✍ Alan F. Thomas; Michel Ozainne 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 German ⚖ 242 KB 👁 1 views

## 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.

Terpenoids Derived from Linalyl Oxide. P

Terpenoids Derived from Linalyl Oxide. Part 1. The stereochemistry of the davanones

✍ Alan F. Thomas; Walter Thommen; Bruno Willhalm; Edward W. Hagaman; Ernest Wenker 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 German ⚖ 371 KB

## Abstract Natural (+)‐davanone is 6__S__,7__S__,10__R__‐2,6,10‐trimethyl‐7,10‐oxidododeca‐2,11‐dien‐5‐one (**1**). Equilibration of davanone with base leads to the four possible isomers, but only a single deuterium atom is exchanged when deuterium oxide is the solvent.