New Methodology for the Stereoselective Synthesis of α‐Furfurylamines from Sugars: Application to the Synthesis of Furyl Amino Acids and 3‐Furylisoserines

Abstract

The synthesis of two new furyl amino acids as rigid isosteres of the dipeptides (D)‐H‐Ser‐(D,L)‐Thr‐OH and (L)‐H‐Ser‐(D,L)‐Thr‐OH is presented. The developed synthetic methodology starts from D‐xylose and D‐arabinose and makes use of trihydroxypropylfurans as intermediates. The key step of the strategy is the introduction of an amino function at the α‐position of the adequate trihydroxypropylfuran derivative. This methodology was also applied to the synthesis of two new (2R,3R)‐3‐furylisoserines as analogues of the C‐13 Taxol/Taxotere side chain.