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

✍ Scribed by Lidia Molina; Elena Moreno-Clavijo; Antonio J. Moreno-Vargas; Ana T. Carmona; Inmaculada Robina

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 301 KB
Volume: 2010
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201000183

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✦ Synopsis

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 (2__R__,3__R__)‐3‐furylisoserines as analogues of the C‐13 Taxol/Taxotere side chain.

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