Formal synthesis of an unusual amino acid component of cyclosporin, involving stereocontrolled nucleophilic 1,4-addition

✍ Scribed by Arounarith Tuch; Michèle Saniìere; Yves Le Merrer; Jean-Claude Depezay

• Book ID: 104361185
• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 700 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00164-x

✦ Synopsis

A syn-(2R)-amino-l,3,4-butanetriol derivative, readily available from Disoascorbic acid, was utilized for the synthesis of MeBmt found in the immunosuppressive undecacyclopeptide cyclosporin. This new strategy involves diastereoselective nucleophilic 1,4-addition of lithium dimethylcuprate to a chiral cx,[3-unsaturated aldehyde, and elaboration of the terminal double bond, by Takai or Wittig method for the MeBmt or its 6Z-isomer, respectively. (~) 1997 Elsevier Science Ltd