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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
Author(s) -
Molina Lidia,
MorenoClavijo Elena,
MorenoVargas Antonio J.,
Carmona Ana T.,
Robina Inmaculada
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000183
Subject(s) - chemistry , stereoselectivity , stereochemistry , amino acid , xylose , arabinose , derivative (finance) , chemical synthesis , combinatorial chemistry , organic chemistry , biochemistry , catalysis , fermentation , financial economics , economics , in vitro
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.