title: Total Synthesis of Nuclear Factor of Activated T-Cells-68 (NFAT-68): Sequential Use of Chiral Allenylsilane and Titanium Alkoxide-Mediated Reductive Coupling Bond Construction.
abstract: Highly enantioenriched chiral allenylsilanes 4 were prepared in high yield through a scalable synthetic sequence, employing a modified copper-catalyzed SN2' reaction. These reagents were used for the production of enantioenriched homoproparglylic ethers 5, which were subjected to titanium alkoxide-mediated reductive coupling with acetylenic esters to produce (E,E)-dienes 6 bearing α,β,γ,δ-unsaturated esters. Both enantiomers of nuclear factor of activated T-cells-68 (NFAT-68) were synthesized in five steps with the sequential use of the two methods.
authors: Department of Chemistry, Metcalf Center for Science and Engineering, Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
authors: Bin
authors: B
authors: Cai
authors: Department of Chemistry, Metcalf Center for Science and Engineering, Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
authors: Ryan W
authors: RW
authors: Evans
authors: Department of Chemistry, Metcalf Center for Science and Engineering, Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
authors: Jie
authors: J
authors: Wu
authors: Department of Chemistry, Metcalf Center for Science and Engineering, Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
authors: James S
authors: JS
authors: Panek
mesh_terms: D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
chemical_list: D006873:Hydroquinones; C094350:NFAT 68; D010087:Oxides; D012821:Silanes; D014025:Titanium