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Transformation of davanone : Reductive cleavage of tetrahydrofuran and thermal cyclization of 1:3-diene

โœ Scribed by Laxmi N. Misra; Amitabh Chandra; Raghunath S. Thakur

Book ID
104229638
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
257 KB
Volume
30
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

a)

Char1wood.B.V. and Banth0rpe.D.V.

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โœ Benjamin Travis; Babak Borhan ๐Ÿ“‚ Article ๐Ÿ“… 2001 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 112 KB

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