The deconstructive ring cleavage
of cyclic thioethers
is achieved
through a Chan–Lam type process with boron compounds. The sequential
hydroboration/ring cleavage process from alkynes offered a new route
to the preparation of vinyl sulfides based on the developed conditions.
Further exploration has demonstrated the versatility of nucleophiles,
delivering various functionalized sulfides featuring linear frameworks.
(S)‐Naproxen was synthesized by the regioselective and stereospecific epoxide ring opening of (2S,3S)‐epoxy‐1‐butanol (2) with diethyl‐2‐(6‐methoxynaphthyl)aluminium (5) as the key step. Thus, treatment of di‐ethylaluminate of 2 with 5 at 0° afforded (2S,3S)‐3‐(6‐methoxy‐2‐naphthyl)butan‐1,2‐diol (6), which was oxidized by sequential treatment with sodium periodate and potassium permanganate in a mixture of tert‐butyl‐alcohol and phosphate buffer (pH 7.0) to give naproxen in high enantiomeric purity.
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1993 carboxylic acids carboxylic acids (naphthalene compounds) Q 0940
-172Synthesis of Naproxen via Regioselective Ring Opening of (2S,3S)-Epoxy-1-butanol.-The key step in the synthesis of the antiinflammatory agent naproxen ( V) is the regio-and stereoselective ring opening of the epoxide (I). -(AHN, K. H.; JIN, C. S.; KANG, D. H.; SHIN, Y. S.; KIM, J. S.; HAN, D. S.; KIM, D. H.; J.
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