4.4 Article

Chemistry of renieramycins. Part 11: Total synthesis of (±)-cribrostatin 4

Journal

TETRAHEDRON
Volume 67, Issue 47, Pages 9185-9192

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.09.076

Keywords

Total synthesis; Marine natural product; Isoquinoline; Cribrostatin 4; Cytotoxicity

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan [23590019, S0801043]
  2. Japan Society for the Promotion of Science (JSPS)
  3. Grants-in-Aid for Scientific Research [23590019] Funding Source: KAKEN

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A 19-step synthesis of (+/-)-cribrostatin 4 (1) from readily available piperazine-2,5-dione derivative 6 is described. The synthesis features the concise construction of a pentacyclic framework, followed by the base-catalyzed epimerization of the C-1 stereo center of aldehyde (11). The results of cytotoxicity studies are also presented. (C) 2011 Elsevier Ltd. All rights reserved.

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