1570184-05-2

Upstream product

• 24850-33-7 allyltributylstanane 
• 397242-80-7 (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole 
• 158349-27-0 (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one 

Relevant academic research and scientific papers

Concise synthesis of bicyclic iminosugarsviareductive functionalization of sugar-derived lactams and subsequent RCM reaction

An efficient method for the synthesis of bicyclic iminosugars has been developed. The strategy is based on the partial reduction of sugar-derived lactams by Schwartz's reagent and tandem stereoselective nucleophile addition dictated by Woerpel's model which affords polyhydroxylated cyclic amines as key intermediates. Introduction of a vinyl or allyl group to the iminosugar produces diene derivatives that can be subjected to the ring-closing metathesis reaction (RCM) to furnish polyhydroxylated pyrrolizidine, indolizidine and quinozilidine derivatives in good to excellent yields. This sequence of reactions has been applied to the formal synthesis of hyacinthacine A2, a polyhydroxylated pyrrolizidine alkaloid.

Sugar-derived cyclic imines: One-pot synthesis and direct functionalization

A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines.