Convenient methods for the synthesis of 1-substituted 3-adamantyl chlorides and bromides (2), 1-adamantylphenols and -cresols (3), and 1-adamantylacetic (6) as well as 1,3-adamantanediacetic (11) acids are described. Several novel derivatives were synthesized from these key intermediates: adamantylcyclohexanols (4) and -cyclohexanones (5) from adamantylphenols (3), and esters (7,12, and 22), amides (13 and 18), thioamides (9 and 16), amidine (10), nitrile (15), and amines (14 and 17) from 1-adamantanecarboxylic (19) and -acetic (6) acids and 1,3-adamantanediacetic acid (11). Some adamantylpyrimidines (24) and -purines (25 and 26) were also prepared. Antiviral activities of the compounds obtained in this work and a series of new 1-adamantyl alkyl ketones synthesized before, together with those of some known adamantane derivatives, were tested in vitro on monolayer culture of chick ambryo fibroblasts against Newcastle disease virus.

A convenient and economical procedure for synthesis of long‐chain 1‐O‐alkyl glyceryl ethers (V) is described. Alkyl glycidyl ethers (II) which were derived from the reaction of alcohols (I) with epichlorohydrin using a phase transfer catalyst were first converted into the corresponding dioxolanes (III) or 1‐O‐alkyl‐2,3‐di‐O‐acetylglycerols (IV). Subsequent hydrolysis of the resultant products provided 1‐O‐alkyl glyceryl ethers (V) in high yields.

Lipids from natural sources consist mainly of saponifiable substances, such as glycerides, along with some unsaponifiable lipids, some of which are ether lipids. Typical ether lipids are monoalkyl ethers of glycerin, also called alkyl/alkenyl glyceryl ethers. Alkyl/alkenyl glyceryl ethers have also been reported in marine organisms and in human feces. Several chemical syntheses of such ether [ipids have been reported. Typical examples are alkyl glyceryl ether formation by the addition reaction of alkyl glycidyl ether and the telomerization reaction of butadiene with glycerin and a transition metal catalyst. Characteristic chemical structures, such as terpene alkyl glyceryl ethers, archaebacterial macrocyclic ether lipids, and glyceryl ethers of condensed cyclic planar molecules, have been obtained as well. Over the past few decades, industry has shown much interest in the chemistry and application of highly branched fatty acids. For example, isostearyl glyceryl ether (GE-IS) with methyl branching in the middle chain was already known, but it is now prepared at an industrial scale by proprietary alkyl glycidyl ether methods. The characteristic behavior of GE-IS toward water, such as formation of water-in-oil emulsions containing large amounts of water and of liquid crystals, has made it applicable for use in hair and skin care cosmetics. Based on these studies and considerations, glycery[ ether lipids, which are rarely investigated, may become one of the most important and useful lipids in the industry. JAOCS 73, 819-830 (1996). KEY WORDS:Ether lipids, GE-IS, glyceryl ether, glycidyl ether, isostearic acid, isostearyl glyceryl ether, liquid crystal, W/O emulsion.Saponification of lipids from tissues and organs of many marine animals results in water-soluble soaps that have high levels of some unsaponifiable substances, which chiefly include hydrocarbons, such as squalene, sterols, and long-chain alcohols with one or more hydroxyl groups (1,2). Typical longchain alcohols that contain one or more hydroxyl groups are particularly present as monoalkyl ethers of glycerin:RO-CH2-CH-CH 2 cyl glycerol, and batyl alcohol as the major constituents in a mixture of free alkyl glyceryl ethers isolated from the sponge Desmapsamma anchorata, harvested in the Gulf of Mexico, and minor components consisted of Cls, Cl9, C20, and Czl alkyl glyceryl ethers (12). They also found that sponges such

Hydrogenation of carboxylic acids to alcohols at low temperature and under low pressure was achieved by using a new catalyst system, a rhenium‐osmium bimetallic catalyst. The most active catalyst was prepared by the reductionof the corresponding metal oxides with hydrogen in the presence of succinic acid. Decanoic acid was hydrogenated to decanol in high conversions at 25∼100 atm and 100∼120°C. Decane was formed as a by‐product by overreduction of the alcohol. The selectivity of alcohol was improved by the addition of thiophene as a modifier of the catalyst.

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