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By Barus C.

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Hv/0 rose bengal 2 - mi) X ^ | k^o' A a ^ base t 0 ( 1 1 0 ) (111) Irradiation of retinyl palmitate (113) with a 150-W high pressure mercury lamp in the presence of thiobenzophenone (114) gave the 1:1 adduct (115) (Yoshioka et aL, 1968). I1H> (115) R-n-C H 1 5 3 1 When exposed to UV light, retinyl acetate (9) in hexane underwent dimeriza­ tion to give the adduct (116) (Mousseron-Canet et aL, 1968; Giannotti, 1968). 44 Fritz Frickel This (4 + 2) adduct (116) has a structure similar to that of one of the components (117) of kitol, a naturally occurring mixture of dimers of retinol (1) (Tsukida and Ito, 1980).

It was also possible to alkylate the anion of the C sulfone (13) with the dimeric allylpalladium π complex (135) in the presence of a large excess of triphenylphosphine, the complex (135) being pre­ pared from prenyl acetate and palladium(II) chloride (Manchand et aL, 1978). 1 5 1 5 5 5 1 5 5 1 5 AcO (13) several steps + OAc (135) The synthesis of retinol (1) by the ( C + C ) method was developed by Huisman et al. (1956; see also Wendler et aL, 1951). The Reformatsky reaction 1 8 2 2. , 1979) with ethyl bromoacetate led to a product that when dehydrated and hydrolyzed gave 4,14-retroretinoic acid (137), which then reacted with phosphorus trichloride to give the acid chloride (138) of (all-£)-retinoic acid (3).

Metabolites Along with the characterization of retinoid metabolites, chemical syntheses were developed that made it possible to carry out detailed investigations of the newly discovered substances in biochemical and pharmacological test systems. Metabolites in which the cyclogeranyl ring was substituted by oxygen functional groups were discovered in different biological systems after the administration of (all-£)-retinoic acid (3), (13Z)-retinoic acid (17), and retinol (1). , 1979). Compound (65) underwent a very rapid acid-catalyzed rearrangement to give the furanoid compound (180) (see Section III).

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Acoustic Pressure Distributions, Chiefly in Reservoirs and in Pipes by Barus C.


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