Reduction acid anhydride synthesis

The two main resin linkers developed so far are shown in Scheme 18, i.e. tris(alk-oxy)benzylamide- 412 and 4-alkoxybenzylamide-type linkers)341 the former being TFA labile and thus fully compatible with Fmoc/tBu and the latter strongly acid labile and correspondingly compatible with Boc/Bzl chemistry. As shown in the case of the tris(alk-oxy)benzaldehyde handle such handles may be introduced into the C-terminal amino acid ester by reductive amination, and after suitable N -protection coupled to amino-functionalized resins (see Scheme 18). Alternatively, the tris(alkoxy)benzaldehyde-functionalized resin, BAL resin, (see Scheme 14) is used to link the C-terminal amino acid ester by reductive amination. To overcome the difficult acylation of the V -arylamino acid ester derivative on resin (best results with 10 equivalent symmetrical anhydrides), synthesis in solution of the C-terminal dipeptide building block containing the amide handle followed by its attachment to the resin has been proposed)341 ... 

Acetonitrile, 407 Acetophenone, 725,729,730 phenylhydrazone, 852 p-Acetotoluidide, 593, 605 Acetoxime, 343 Acetylacetone, 861, 862, 863 Acetylation, reductive, 749 Thiele, 749 Acetyl chloride, 367 2-Acetylcyciohexanone, 862, 864 Acetylene, 245, 897 reactions of, 245, 246 Acetylenic compounds, synthesis of, 467-469, 895-902 Acetylglycine, 909 Acetylmethylurea, 968, 969 Acetylsalicylio acid, 996 Acetyl-o-toluidide, 578 2-Acetylthiophene, 837 Acid anhydrides of aliphatic carboxylic acids, 371... 

Haworth phenanthrene synthesis. Acylation of aromatic compounds with aliphatic dibasic acid anhydrides to (i-aroylpropionic acids, reduction of the carbonyl group according to Clemmensen or Wolff-Kishner procedures, cyclization of the y-arylbutyric acid with 85% sulfuric acid, and conversion of the cyclic ketone to polycyclic hydroaromatic and subsequently to aromatic compounds. 

Interest in the structure-activity relationships of the gibberellins has led to the partial synthesis of the four stereoisomers about positions 5 and 6 of the hexa-hydrofluorene (57). The unsaturated acid anhydride (56) was prepared by the benzilic acid ring-contraction of the 6,7-diketones obtained from oxidation of desisopropyl dehydroabietic acid, and converted into the saturated acids by reduction and base-catalysed epimerisation. 

The direct synthesis of cantharidin by a Diels-Alder reaction of furan with dimethyl maleic anhydride 6 is not possible. However, cycloaddition can be carried out with 2,5-dihydrothiophene-3,4-dicarboxylic acid anhydride 8 as dienophile. The cycloadduct 9 exolendo mixture 85 15) is subsequently hydrogenated and the tetrahydrothiophene ring in 10 is cleaved by a reductive desulfurization [17] ... 

In 1975, Kellyprepared and characterized a number of polyesters based on 2,5-disubstituted furans in various states of reduction. In this study, 2,5-disubstituted-furan, -dihydrofuran, and -tetrahydrofuran monomers were polymerized using solution, melt-transesterification, ring-opening, and interfacial techniques. These monomers included diacids, diols, diacid chlorides, diesters, dicarboxylic acid anhydrides, as well as monomers based on 5-hydroxymethyl-2-furoic and tetrahydrofuroic acids and esters, and bycyclic lactones containing the tetrahydrofuran ring. A thorough review of previous work done in the area of poljnner synthesis, based on 2,5-disubstituted furan derivatives is reported. It is reported that when... 

This synthesis is related to an earlier sequence that produced lactone 5.20 by reduction of anhydride 5.79, H which was formed by treating N-Cbz aspartic acid... 

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