Intramolecular Tandem seleno-Michael/Aldol Reaction - Novel Strategy in Carbasugars Synthesis

Abstract

: Carbasugars are a wide group of carbohydrate mimetics in which the ring oxygen is replaced by a methylene group. The high importance of these compounds is related to their interesting biological and pharmacological properties which are the matter of current studies. In our work, a concise synthesis of carbasugars from naturally occurring D -pentoses is presented. The one-pot seleno-Michael reaction connected with intramolecular aldol reaction is a key step of the carbasugar core asymmetric synthesis. Further transformation of obtained carbasugar moiety led to different bioactive compounds. Tandem seleno-Michael reaction conjugated with oxidation/elimination step of in situ generated nucleophile was described a few years ago in the intermolecular variant. In our work, we present the first example of this reaction in an intramolecular way which leads to a previously inaccessible cyclic product of Morita–Baylis– Hillman reaction. Conducted experiments allowed us to obtain cyclic products with high yields and good diastereoisomeric excesses.