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Oxidative cyclization of 1,4-dienes to yield 2,3,5-trisubstituted tetrahydrofuran-diols

โœ Scribed by Benjamin Travis; Babak Borhan

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
112 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

KMnO 4 and OsO 4 catalyze the oxidative cyclization of 1,4-dienes to provide 2,3,5-trisubstituted tetrahydrofuran-diols in 30% yield. This reaction proceeds stereoselectively via a proposed [3+2] cycloaddition. Competing oxidative pathways are the major non-productive processes that reduce the yield of the reaction; however, four stereogenic centers are established in one-step.

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Enantioselective cyclization of chiral b
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
โœ M.M. Ponpipom; R.L. Bugianesi; J.C. Chabala ๐Ÿ“‚ Article ๐Ÿ“… 1988 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 264 KB

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