Brominated bicyclic sesquiterpenes of the chamigrene ring system are cOnnmOn metabolites found in many species of the marine red alga Laurencia 1 . The biosynthesis of these compounds has been generally predictedA\*' to involve the intermediacy of a brominated monocycle-farnesol derivative in analog
α-bromocuparene and α-isobromocuparene, new bromo compounds from laurencia species
✍ Scribed by Teruaki Suzuki; Minoru Suzuki; Etsuro Kurosawa
- Publisher
- Elsevier Science
- Year
- 1975
- Tongue
- French
- Weight
- 119 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
In recent years, the brominated or non-brominated laurane-type sesquiterpenoids have been isolated from seaweeds of genus Laurencia (l-4). Our further investigations of neutral essential oil from Laurencia species have led to the isolation of two new bromo compounds, a-bromocuparene (I) and a-isobromocuparene (II) from &. glandulifdra Blitzing, and II from &. nipponica Yamada, on the chromatography over neutral alumina with n-hexane. The compounds, I and II, appeared to be the first recognized cuparane-type sesquiterpenoid from seaweeds and the former seems to be the biogenetical precursor of laurene (III) (I), closely related to cuparane-type sesquiterpenoids.
📜 SIMILAR VOLUMES
An extensive study of the neutral essential oil from Laurencia nipoonica Yamada (Rhodomelaceae; Urasozo in Japanese)(2) led to isolation of a new bromo alcohol and its acetate in 0.02 and 0.0005$ yields, respectively. They are designated as laurefucin and acetyllaurefucin and are assigned structures
Facile Syntheses of α-Bromo-α-silyl Ketones and α-Bromoacylsilanes from tert-Butyldimethylsilyldibromomethane and Carbonyl Compounds. -The synthesis of title compounds such as (III) and (V) and their usefulness is shown. The Tbs-group plays a critical role in the formation of these products. Mechan