Asymmetric Synthesis of (+)-Polyoxamic Acid via an Efficient Organocatalytic Mannich Reaction as the Key Step

Abstract

A short and efficient stereoselective synthesis of (+)-polyoxamic acid is described using an organocatalytic asymmetric Mannich reaction as the key step. The reaction proceeded in high yield and with excellent selectivity to establish two out of the three stereocenters present in (+)-polyoxamic acid. Additional steps include a diastereoselective reduction and ozonolysis of the furyl ring to generate the corresponding carboxylic acid.

(+)-polyoxamic acid - Mannich reaction - organocatalysis - diastereoselective reduction - ozonolysis

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