Unsaturated amino alcohols structures

Apart from the chemistry of these pyrrolizidine alkaloids, their physiological effects, in particular their hepatotoxicity, have been investigated in depth by the CSIRO Division of Animal Health, as a result of which it has been possible to establish correlations between activity and structure liver damage is caused by alkaloids such as 90 or 91 because unsaturated amino alcohols of this type, which are esterified on one or both hydroxyl groups, undergo metabolism in the liver to form the toxin 93 this substance is immediately responsible for the mutagenic and carcinogenic effects observed [106, 107], which include... 

Garrido, L., Zubia, E., Ortega, M.J., Naranjo, S., and Salva, J. (2001) Obscuraminols, new unsaturated amino alcohols from the tunicate Pseudodistoma obscurum structure and absolute configuration. Tetrahedron, 57, 4579-4588. 

The stereochemical course of reduction of imonium salts by Grignard reagents was found to depend on the structure of the reagent 714). Hydro-boration of enamines and oxidation with hydrogen peroxide led to amino-alcohols (7/5). While aluminum hydrogen dichloride reacted with enamines to yield mostly saturated amines and some olefins on hydrolysis, aluminum hydride gave predominantly the unsaturated products 716). 

Figure 12.11 Phosphoglyceride structure. The members of this group are derivatives of the parent compound, l,2-diacyl-src-glycerol-3-phosphate (phosphatidic acid) in which X is a hydrogen atom. This is replaced by either an amino alcohol or a polyhydroxy residue. In phosphoglycerides derived from animal tissues R1 is usually a saturated acyl chain of between 16 and 20 carbon atoms and R2 is usually unsaturated. Polyunsaturated acyl chains containing 16 or 18 carbon atoms predominate in leaf phosphoglycerides and those of bacterial origin are often more complex.

The structure proposed for septicine (20), the dehydroindolizidine constituent of Ficus septica, has recently been confirmed by two independent syntheses. The first synthesis proceeded from veratraldehyde, which was condensed with homoveratric acid to give the unsaturated acid (21) this was then converted into the primary chloride (22) by standard methods. Alkylation of L-prolinol with this chloride gave the amino-alcohol (23), which was converted into its O-methanesulphonate ester. Reaction of this ester with sodium hydride in anhydrous... 

There are few reports of successful one-step synthesis of primary diamines, and the examples are limited to amines with a special structure. Amination of 1,4-cy-clohexanediol in supercritical ammonia (135 bar) over a Co-Fe catalyst alforded 67 % 1,4-diaminocyclohexane [21]. Excess ammonia, as both supercritical solvent and reactant, and short contact time in the continuous fixed-bed reactor favored the desired reactions. In the best example the cumulative selectivity for the diamine and the intermediate amino alcohol was 97 % at 76 % conversion. Recycling of the unreacted diol and amino alcohol can provide an alternative to the eurrent process, the hydrogenation of pnra-phenylenediamine. The high seleetivity was because of the rigid structure and the relative positions of OH functionality in the substrate. For comparison, amination of 1,4-butanediol under similar conditions yielded pyiTolidine as the major product 1,4-diaminobutane was barely detectable. When 1,3-cyclohexanediol was aminated with the same catalyst in the continuous system, the yield of 1,3-diaminoeyclohexane dropped below 5%, mainly because elimination of water led to undesired monofunctional products via a,/9-unsaturated alcohol, ketone, and/or amine intermediates [22]. 

Chiraldex B-PH Structural isomers, unsaturated no aromatie eompounds. Linear and cyclic amines and alcohols, acids, lactones, amino aleohols, sugars, bicyclic compounds and epoxides. 

Sphingosine is an unsaturated aminodiol, dihydroxyaminooctadecen (Levene 1913/14, Klenk 1929). The correct structure with the relative positions of the amino- and alcoholic groups and the stereochemistry corresponds to that given in the following formula (Carter et al. 1942, 1947) and Stuart-model ... 

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