Total Synthesis of GKK1032A2 via Direct 13‐Membered Macrocyclization Using a Nucleophilic Aromatic Substitution of an (η6‐Arene)Chromium Complex. Issue 6 (23rd February 2017)

• Record Type: Journal Article
• Authors: Sugata, Hayato; Inagaki, Kensuke; Ode, Toshiaki; Hayakawa, Tomoki; Karoji, Yuki; Baba, Motoaki; Kato, Ryo; Hasegawa, Daiju; Tsubogo, Tetsu; Uchiro, Hiromi
• Is Part Of: Chemistry, an Asian journal. Volume 12:Issue 6(2017)
• Page Start: 628
• Page End: 632
• Publication Date: 2017-02-23
• Subjects: aromatic substitution -- gkk1032a2 -- macrocycles -- Pi interactions -- total synthesis; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201601728
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: The first enantioselective total synthesis of GKK1032A2 has been achieved. The key step is a direct construction of the highly strained 13‐membered macrocycle of GKK1032A2 by an intramolecular nucleophilic aromatic substitution (SN Ar) reaction. This is the first successful example of construction of a macrocycle with an aryl ether linkage utilizing an intramolecular SN Ar reaction of an ( η 6 ‐arene)chromium complex. Abstract : Lucky number 13 ! The enantioselective total synthesis of GKK1032A2 has been achieved. The key step is a direct construction of the highly strained 13‐membered macrocycle of GKK1032A2 by an intramolecular nucleophilic aromatic substitution (SN Ar) reaction. This is a successful example of construction of a macrocycle with an aryl ether linkage utilizing an intramolecular SN Ar reaction of an ( η 6 ‐arene)chromium complex.