Polyhydroxyamino‐Piperidine‐Type Iminosugars and Pipecolic Acid Analogues from a <scp>D</scp>‐Mannose‐Derived Aldehyde

Abstract

Abstract A general strategy for the synthesis of diversely substituted 3,4,5‐trihydroxypiperidines (including two natural products), 5‐amino‐3,4‐dihydroxypiperidines, 3,4,5‐trihydroxypipecolic acids, and 2‐(aminomethyl)‐3,4,5‐trihydroxypiperidines is reported. The procedure used a double reductive amination or a Strecker reaction, starting from differently protected aldehydes readily synthesized on a gram scale from D ‐mannose. The biological activities of the target compounds were evaluated, and some of them showed moderate inhibition of α‐ L ‐fucosidase and β‐glucosidase.