SYNTHESIS OF NAPROXEN VIA REGIOSELECTIVE RING-OPENING OF (2S,3S)-EPOXY-1-BUTANOL
SCIE
SCOPUS
- Title
- SYNTHESIS OF NAPROXEN VIA REGIOSELECTIVE RING-OPENING OF (2S,3S)-EPOXY-1-BUTANOL
- Authors
- AHN, KH; HAN, DS; JIN, CS; KANG, DH; KIM, DH; KIM, JS; SHIN, YS
- Date Issued
- 1993-05
- Publisher
- BLACKWELL PUBLISHING LTD
- Abstract
- (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 diethylaluminate of 2 with 5 at 0-degrees 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.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/22072
- DOI
- 10.1002/jhet.5570300337
- ISSN
- 0022-152X
- Article Type
- Article
- Citation
- JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 30, no. 3, page. 825 - 827, 1993-05
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