A sulfoxide-stabilized anion in a synthesis
المؤلف:
Jonathan Clayden , Nick Greeves , Stuart Warren
المصدر:
ORGANIC CHEMISTRY
الجزء والصفحة:
ص661
2025-07-02
527
A sulfoxide alkylation formed the key step of a synthesis of the important vitamin biotin. Biotin contains a five-membered heterocyclic sulfide fused to a second five-membered ring, and the bicyclic skeleton was easy to make from a simple symmetrical ester. The vital step is a double SN2 reaction on primary carbon atoms.
The next step was to introduce the alkyl chain—this was best done by first oxidizing the sulfide to a sulfoxide, using sodium periodate. The sulfoxide was then deprotonated with n-BuLi and alkylated with an alkyl iodide containing a carboxylic acid protected as its tert-butyl ester. Reduction of the sulfoxide and hydrolysis back to the free acid gave biotin.
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