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Structure and absolute configuration of a new rearranged chamigrane-type sesquiterpenoid from the sea hare Aplysia sp.
β Scribed by Sergei N Fedorov; Larisa K Shubina; Anatoly I Kalinovsky; Ekaterina G Lyakhova; Valentin A Stonik
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 145 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
6S,10S)-3,10- Dimethyl-7,11-dimethylidenespiro[5,5]undec-2-en-4-one (1), a new rearranged chamigrane-type sesquiterpenoid with two sp 2 -hybridized carbons in Ξ±-positions to the spiro-atom, was isolated from the alcoholic extract of the sea hare Aplysia sp. and its structure and absolute configuration were established by chemical transformations, NMR, EIMS, IR, UV and CD spectroscopy.
π SIMILAR VOLUMES
Four new halogenated chamigrenes have been isolated from the sea hare, the (E)-and (Z)-9-(bromomethylidene)-1,2,5-trimethylspiro[5.5]undeca-l,7-dien-3-ones (11 and 10, resp.) the structures of which were deduced by NMR spectroscopy and by comparison with a known relative, the (8R,9R)-8-bromo-9-chlor