Abstract
5-Substituted lactol 1 was converted to 2,5-disubstituted tetrahydrofuran derivatives by a Lewis acid-promoted reaction with allylsilanes. High trans selectivity (12:1) was obtained when hindered allylsilane 8 was employed. 5-Substituted lactol 16 was transformed into 2,5- cis-disubstituted tetrahydrofuran 17b (6:1 ratio) by a TiCl 4-promoted intramolecular allyl transfer process. Additionally, 2,5- cis-disubstituted tetrahydrofuran derivatives were obtained in good yields and diastereoselectivities after alkyllithium addition to lactone 6, followed by Et 3SiH/BF 3·OEt 2 reduction of the corresponding hemiketals.
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