Total synthesis of steroid hormones

Camphor was a scarce and expensive natural product with a worldwide demand. [ when? ] [ according to whom? ] Haller and Blanc synthesized camphor from camphor acid; [ when? ] [2] however, the precursor, camphoric acid, was of unknown structure. When Finnish chemist Gustav Komppa synthesized camphoric acid from diethyl oxalate and 3,3-dimethylpentanoic acid in 1904, the structure of these precursors allowed chemists at the time to infer the complicated ring structure of camphor. Shortly thereafter, [ when? ] William Perkin published another synthesis of camphor. [ relevant? – discuss ] The work on the total chemical synthesis of camphor allowed Komppa to begin industrial production of this compound, in Tainionkoski, Finland , in 1907.

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An additional stereogenic center is created when 1 and 2 are combined. Initial attempts to carry out the condensation gave the wrong stereochemical outcome, as Pictet-Spengler condensation preceded tosylate displacement. To work around this problem, 1 and 2 were combined in the presence of cyanide ion, to give 15 . Heating of 15 gave cyclization, but again to the wrong diastereomer, perhaps because in the intermediate ion pair from cyanide ionization, the cyanide ion was blocking one face of the intermediate cation. Fortunately, on stirring at room temperature in aqueous HCl, 15 did cyclize to the correct diastereomer, providing, after acylation, reserpine ( 3 ).

Total synthesis of steroid hormones

total synthesis of steroid hormones


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