A glycal based synthesis of (+)-bulgecinine, 3-hydroxy-2,5-dihydroxymethylpyrrolidine and 2-oxapyrrolizidin-3-ones proceeding through a common intermediate is reported. The key step in the work presented here is a two-step conversion of 4,6-di-O-benzyl-d-glucal to 2,3-dideoxy-2-tosylamido-d-glucose. This manuscript reports the first carbohydrate based approach to the synthesis of (+)-bulgecinine and the whole sequence has been accomplished with complete stereochemical integrity without the formation of mixture of products in any of these steps.
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| http://dx.doi.org/10.1016/j.carres.2020.107931 | DOI Listing |
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