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An enantioselective synthesis of (+)-biotin 1 starting from naturally available cysteine is described. The key steps are the unusual stereochemical outcome of radical cyclization of compound 10 to prepare 5,5-fused system 11, and the introduction of C4-sidechain at C 6 in 13 via a Grignard reaction.
The condensation of arylacetonitriles with cyclic ketones using aqueous NaOH or KOH under phase transfer catalysis gives almost quantitative yields of cycloalkanols. This protocol is utilized for a practical synthesis of the antidepression drug, venlafaxine 1.
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