Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of delta-trialkylsilyloxy substituted ketones: total synthesis of (-)-centrolobine |
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| Authors: | Evans P Andrew Cui Jian Gharpure Santosh J |
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| Affiliation: | Department of Chemistry, 800 East Kirkwood Avenue, Indiana University, Bloomington, Indiana 47405, USA. paevans@indiana.edu |
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| Abstract: | ![]()
[reaction: see text] The stereoselective intramolecular reductive etherification of delta-trialkylsilyloxy substituted ketones with catalytic bismuth tribromide and triethylsilane provides a convenient method for the construction of cis-2,6-disubstituted tetrahydropyrans. This method was highlighted in the key step of an expeditious total synthesis of the antibiotic, (-)-centrolobine. |
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