Analog synthesis

An analogous synthesis of benzofurans from O-aryloximes has been exemplified, but not investigated in any detail (Scheme 39e) (66TL5225,67TL2867,73KGS31). 

The dl-pukateine methyl ether obtained in small yield in the analogous synthesis was isolated as the hydriodide and resolved by the successive use of d- and 1-tartaric acids into the 1-base, m.p. 136°, [a]ff° — 252° (EtOH), identical with the methyl ether of pukateine, and the d-base, m.p. 136°, [a] " -f 256-4° (EtOH). 

W. Pfleiderer, H. Schirmeister, T. Reiner, M. Pfister, and R. Charubala, Biophosphates and Their Analogs-Synthesis, Structure, Metabolism and Activity, Bioact. Mol. 3, 133(1987). 

Figure 10.25 Inverted approach for aldose synthesis using FruA catalysis, and application ofthe strategy for deoxysugar synthesis based on a phosphorothioate analog synthesis of 1-deoxysugars by FSA catalyzed addition of hydroxyacetone.

J.G. Topliss, Application of operational schemes for analog synthesis in drug design. J. Med. Chem., 15 (1972) 1001-1011. 

An analogous synthesis of Z-protected peptide esters is described in reference [47]. The reaction conditions were heating for several hours in anhydrous xylene at 140 °C. 

An analogous synthesis, via its menthydrazone (59), of optically active (+)-/>-(cyclohexylmethyl-l-naphthylstannyl) acetophenone, (+)-(55), which is characterized... 

Langston, J. W., Ballard, P., Tetrud, J. W. and Irwin, I. Chronic Parkinsonism in humans due to a product of meperidine-analog synthesis. Science 219 979-980,1983. 

In this route a dihydroisoquinoline (58) is N alkylated with a highly functionalized o -bromoacetophenone (59) to give a quaternary salt (60), which is treated with base and cyclizes to a pyrroloisoquinoline (60). The pyrrole nucleus is then formylated under Vilsmeier-Haack conditions at position 5 and a proximate mesylated phenolic group is deprotected with base to yield a pen-tasubstituted pyrrole (61). Subsequent oxidative cyclization of this formylpyr-role produces the 5-lactone portion of lamellarin G trimethyl ether (36). This sequence allows for rapid and efficient analog synthesis as well as the synthesis of the natural product. 

P. Vogel, S. Gerber-Lemaire and L. Juillerat-Jeanneret, Imino -C- disaccharides and analogs synthesis and biological activity, in Imino sugars, from synthesis to therapeutic applications, ed. P. Compain and O. Martin, Wiley, 2007, pp. 87-130. 

S. D., Lucas, B.J., Gardell, S.J., Lyle, E.A., Appleby, S.D., Cook, J.J., FIolahan, M.A., Stranieri, M.T., Lynch,Y J., Lin, J.H., Chen, I.W., Vastag, K., Naylor-Olsen, A.M., and Vacca, J.P. Discovery and development of the novel potent orally active thrombin inhibitor N-(9-Hydroxy-9-fluorenecarboxy)prolyl tran s -4-amin ocycl ohexylmethyl ami de (L-372,460) coapplication of structure-based design and rapid multiple analog synthesis on solid support. 

Optimization of biological properties in a series of miticidal and mite ovicidal 2-aryl-l,3-cycloalkanediones, Ia,b, and enol esters, II, was achieved through analog synthesis and testing supported by the development of quantitative structure/ activity trends during the course of the project. QSAR equations developed during an initial phase provided the basis for both... 

Convenient preparative access to such chiral euninocyclitols as should facilitate chemical analog synthesis and biochemical muta-synthesis in the field of 2uninocyclitol antibiotics. A short and economical synthesis of and its hitherto unknown IL-(1,3,4,5/2), or D-epi, stereoisomer was therefore devised (7). It is based on the nitroalkane cyclization method (8), and is delineated in Figure 1. 

Betanechol Betanechol, 2-carbamoyloxy-l-(A,A,iV-trimethyl)propyl ammonium chloride (13.1.8), is made by either the subsequent reaction of l-(iV,A,A-trimethylammonium) propan-2-ol with phosgene, followed by ammonia, or by a completely analogous synthesis of carbachol by the reaction of l-chloro-2-propanol with phosgene followed by consequent reactions with ammonia, and then with trimethylamine, giving betanechol (13.1.8) [14,15],... 

A similar strategy can also be applied for the analogous synthesis of naphthyridine derivatives [93]. Here A-allyl derivatives of o-aminobenzaldehyde,... 

G. Synthesis of Emetine Analogs Synthesis of Indole Alkaloid Analogs... 

Vilsmeier formylation of carbazole can be conducted to give good yields of 3-monoformylcarbazoles 9-methyl, 9-ethyl, 9-n-butyl, 9-isoamyl, and 9-isobutyl derivatives were made in this way. The C-form-ylation of various carbazoles required for alkaloid and alkaloid analog synthesis makes instructive reading 1,4-dimethyl-, - 1,4,6-trimethyl-, - 1,4,9-trimethyl-, 1,4-diraethyl-6,7-methylenedioxy-, l,4-dimethyl-6,7-dimethoxy-, l,4-dimethyl-8-methoxy- (some N-formylation also obser-... 

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