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Terpenes and terpene derivatives, XXIV. Isolation and stereochemistry of the four artedouglasia oxides

✍ Scribed by Weyerstahl, Peter ;Marschall-Weyerstahl, Helga ;Schröder, Martin ;Kaul, Vijay K.

Publisher
John Wiley and Sons
Year
1988
Tongue
English
Weight
188 KB
Volume
1988
Category
Article
ISSN
0947-3440

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✦ Synopsis

Froni thc cssential oil of Arfmiisiu lacinida the four stereoisonicrs of artedouglasia oxide 2a-d could be isolated. Analysis uf the high-resolution 'H-NMR smtra and comparison with dnvsnonc ( I ) allnwcd thc stcrcochemicaf assignment.

Davanone (1) is the main component of the essential oil of Artemisia pallens (davana oil) and an important constituent of some other oils2). The stereochemistry of 1 was proven by Thomas3) and two stereoselective syntheses were published4). In 1974, Thomas 5, isolated from the same davana oil an oxidized, cyclized derivative of 1, the 2,6,6-trimethyl-2-(tetrahydro-5-methyl-5-vinyl-2-furyl)-2Hpyran-3(6H)-one (2). He suggested a cis substitution at the tetrahydrofuran ring, but there was no certainty. Eight years later Bohl-mann6' isolated from the aerial parts of A. douglasia a compound with the same structure, but also with unknown stereochemistry. He named this ketone artedouglasia oxide.

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