4.6 Article

Short Syntheses of 4-Deoxycarbazomycin B, Sorazolon E, and (+)-Sorazolon E2

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 12, Issue 12, Pages 1305-1308

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201700471

Keywords

C-C coupling; enantioselective synthesis; hydroxycarbazoles; sorazolons; vanadium

Funding

  1. JSPS KAKENHI [JP16K08163, JP16H01152, JP17H05373]
  2. JST Advance Catalytic Transformation Program for Carbon Utilization (ACT-C) [JPMJCR12YK]
  3. Grants-in-Aid for Scientific Research [17H05373, 16K08163, 16H01152] Funding Source: KAKEN

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Short syntheses of 4-deoxycarbazomycin B and sorazolon E were established through the condensation of cyclohexanone and commercially available 4-methoxy-2,3-dimethylaniline, followed by Pd-II-catalyzed dehydrogenative aromatization/intramolecular C-C bond coupling and deprotection. A chiral dinuclear vanadium complex (R-a,S,S)-6 mediated the enantioselective oxidative coupling of sorazolon E, affording (+)-sorazolon E2 in good enantioselectivity.

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