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Chapter 21: Q35-f. (page 1126)
Show how you would synthesize each compound, starting with an ester containing nomore than eight carbon atoms. Any other necessary reagents may be used.
f.
The synthesis of the given compound is given below.
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An ether extraction of nutmeg gives large quantities of triolein, a waxy crystalline solid of melting point 57 °C. The IR spectrum of triolein shows a very strong absorption at1735 cm-1 . Basic hydrolysis of triolein gives 1 equivalent of glycerol and 3 equivalents of oleic acid ((9Z)-Octadec-9-enoic acid).
(a) Draw the structure of triolein.
(b) Predict the products formed when triolein is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts.
Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.
(c) phthalic acid monoamide
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(a) ethyl propionate
(b)phenyl 3-methylhexanoate
(c)benzyl benzoate
(d)cyclopropyl cyclohexanecarboxylate
(e)tert-butyl acetate
(f) diallyl succinate
Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.
Macrolide antibiotics, including erythromycin and azithromycin (), contain a large ring lactone. One of the largest ever reported is Gargantulide A, the structure of which was determined by the research group of Prof. William Gerwick of the Scripps Institution of Oceanography (Organic Letters, 2015, 17, 1377–1380). Isolated from a Streptomyces bacterium, it kills pathogenic bacteria like MRSA and Clostridium difficile, but it proved too toxic to the test animals to continue further testing.
(a) Identify the lactone that makes this a macrolide structure.
(b) How many rings does this structure contain? How many atoms are in the largest ring?
(c) Many complex NMR experiments were used to determine the stereochemistry of most, but not all, of the chiral centers. How many chiral centers does the structure contain?
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