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Enantioselective cyclization of chiral butane-1,4-diols to chiral tetrahydrofurans: synthesis of chiral trans-2-(3-methoxy-5-methylsulfonyl-4-propoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (L-659,989), a potent PAF-receptor antagonist

✍ Scribed by M.M. Ponpipom; R.L. Bugianesi; J.C. Chabala

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 264 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)82307-2

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✦ Synopsis

Acid catalyzed cyclization of (lR,4RS)-and (lS,4RS)-l-(3-methoxy-5-methylsuHonyl-4-propoxypheny~~-(3,4,5trimethoxyphenyl)butane-1,4-diols to the corresponding chiral cis-and trans-tetrahydrofurans proceeds with retention of configuration at C-l. Using this stereo-and regioselective reaction, the two optically active enantiomers of L-659,969, a potent PAF-receptor antagonist, were prepared.