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Scopine is a 
tropane alkaloid
Tropane alkaloids are a class of bicyclic .2.1alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloid ...
found in a variety of plants including '' Mandragora'' root, '' Senecio mikanioides'' (''Delairea odorata''), ''Scopolia carniolica
''Scopolia carniolica'', the European scopolia or henbane bell, is a poisonous plant belonging to the family Solanaceae. It has dark violet flowers on long hanging stems. It grows to in height. Its toxicity derives from its high levels of tropan ...
'', and '' Scopolia lurida''.
Scopine can be prepared by the hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolys ...
of scopolamine. It can also be prepared in three steps from ''N''-methoxycarbonylpyrrole and 1,1,3,3-tetrabromoacetone; the reagents are combined in a +3cycloaddition
In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity". T ...
, followed by a diastereoselective
In stereochemistry, diastereomers (sometimes called diastereoisomers) are a type of stereoisomer. Diastereomers are defined as non-mirror image, non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have dif ...
reduction with diisobutylaluminum hydride
Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a reducing agent with the formula (''i''-Bu2AlH)2, where ''i''-Bu represents isobutyl (-CH2CH(CH3)2). This organoaluminium compound is a reagent in organic synthesis.
Properties
Lik ...
, and finally a Prilezhaev epoxidation with trifluoroperacetic acid
Trifluoroperacetic acid (trifluoroperoxyacetic acid, TFPAA) is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula . It is a strong oxidizing agent for organic oxidation reactions, such ...
affords scopine.
See also
*Aposcopolamine
Aposcopolamine (apohyoscine) is a bio-active isolate of '' Datura ferox'' and several species of ''Physochlaina'',Gorinova, N.I., Atanassov, A.I. and Velcheva, M.P. ''In Vitro Culture and the Production of Physochlaine and Other Tropane Alkaloids' ...
* Umbelliferone
Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and ''beta''-umbelliferone, is a natural product of the coumarin family.
It absorbs ultraviolet light strongly at several wavelengths. There are some indications that this ch ...
References
{{reflist Tropane alkaloids Tropane alkaloids found in Solanaceae Epoxides Heterocyclic compounds with 1 ring