Concise Synthesis of All Stereoisomers of Dendroamide A by Fluorous Mixture Synthesis Based on Fluorous‐Fmoc Protection of Amino Acids1. Issue 18 (15th May 2015)

• Record Type: Journal Article
• Authors: Takahashi, Hiroaki; Endo, Natsuki; Takanose, Hitomi; Sugiyama, Yuya; Eguchi, Fumitaka; Oguri, Kazuma; Hamamoto, Hiromi; Shioiri, Takayuki; Matsugi, Masato
• Is Part Of: European journal of organic chemistry. Issue 18(2015)
• Page Start: 3971
• Page End: 3982
• Publication Date: 2015-05-15
• Subjects: Synthetic methods -- Combinatorial chemistry -- Total synthesis -- Natural products -- Fluorine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500394
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A liquid‐phase split‐type synthesis of all the stereoisomers of dendroamide A, which exhibits multidrug‐resistance reversing activity, has been carried out. The key to the concise synthesis was the fluorous‐Fmoc protection strategy of each of the starting materials (D ‐ andL ‐alanine andD ‐ andL ‐valine). By using the fluorous‐Fmoc encoding method, the target stereoisomers were effectively synthesized individually in fewer steps than by the corresponding linear synthetic routes. Abstract : All eight stereoisomers of dendroamide A have been concisely synthesized by fluorous mixture synthesis based on an encoding strategy of amino acid stereocenters by using fluorous‐Fmoc reagents.