4.4 Article

Total synthesis of makaluvamine A/D, damirone B, batzelline C, makaluvone, and isobatzelline C featuring one-pot benzyne-mediated cyclization-functionalization

Journal

TETRAHEDRON
Volume 68, Issue 46, Pages 9376-9383

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.09.034

Keywords

Alkaloid; Benzyne; Cyclization; One-pot reaction; Pyrroloquinoline

Funding

  1. Cabinet Office, Government of Japan [LS008]
  2. Ministry of Education, Culture, Sports, Science, and Technology, Japan
  3. KAKENHI [19890014, 21790006, 23790004]
  4. Tohoku University
  5. Nagase Science and Technology Foundation
  6. Suntory Institute for Bioorganic Research
  7. Astellas Foundation for Research on Metabolic Disorders
  8. Banyu Life Science Foundation International
  9. Grants-in-Aid for Scientific Research [19890014, 23790004, 21790006] Funding Source: KAKEN

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Total synthesis of pyrroloquinoline alkaloids, such as makaluvamine AID, damirone B, batzelline C, makaluvone, and isobatzelline C, was achieved featuring a one-pot benzyne-mediated cyclization-functionalization reaction. The synthetic utility was demonstrated by the construction of the common pyrrolo[4,3,2-de]quinoline skeleton. (C) 2012 Elsevier Ltd. All rights reserved.

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