✦ LIBER ✦
Terpenes and Terpene Derivatives, XXX. Isolation and Synthesis of Isohumbertiol, the First Naturally Occurring Sesquiterpene Alcohol with a Humbertiane Skeleton
✍ Scribed by Weyerstahl, Peter ;Christiansen, Christian ;Marschall, Helga
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 353 KB
- Volume
- 1992
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
From Vassoura oil (Baccharis dracunculifolia DC.) the four isomeric isohumbertiols A–D (7–10), the first naturally occurring sesquiterpene alcohols with a humbertiane skeleton could be isolated and assigned unambiguously by establishing a correlation with the known cabreuva oxides A–D (3–6). Reaction of the ketone (+)‐16 with vinylmagnesium bromide gave a mixture of the isohumbertiols B and D [(+)‐8 and ent‐10]. Treatment of 8/10 with SnCl~4~ furnished the tetraline derivative 18, whereas with hydrochloric acid the cabreuva oxides B and D (4 and 6) were obtained.