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Anhydrous tin(II) chloride is an efficient catalyst for the reaction of epoxides with acetone to prepare 2,2-dimethyl-1,3-dioxolanes (acetonides) in good to excellent yields. Mono-, di-, and trisubstituted epoxides participate equally well in this diastereospecific reaction. The use of single enantiomer epoxides under the reported conditions results in significant erosion of optical activity.

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On northeastern Pacific coasts, Ulvaria obscura is a dominant component of subtidal "green tide" blooms, which can be harmful to marine communities, fisheries, and aquaculture facilities. U. obscura is avoided by herbivores relative to many other locally common macrophytes, which may contribute to its ability to form persistent blooms. We used a bioassay-guided fractionation method to experimentally determine the cause of reduced feeding on Ulvaria by echinoderms, molluscs, and arthropods. Our results indicated that dopamine, which constituted an average of 4.4% of the alga's dry mass, was responsible for decreased feeding by sea urchins (Strongylocentrotus droebachiensis). Subsequent experiments demonstrated that dopamine also reduced the feeding rates of snails (Littorina sitkana) and isopods (Idotea wosnesenskii). Dopamine is a catecholamine that is a common neurotransmitter in animals. The catecholamines dopamine, epinephrine (adrenaline), and norepinephrine also occur in at least 44 families of higher plants. The functions of catecholamines in plants are less well known than in animals but are likely to be diverse and include both physiological and ecological roles. Our results are the first experimental demonstration of a plant or algal catecholamine functioning as a feeding deterrent. This novel use of dopamine by Ulvaria may contribute to the formation and persistence of harmful Ulvaria blooms in northeastern Pacific coastal waters.

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