4.4 Article

Concise synthesis of the DEFG ring system in rubriflordilactone B

Journal

TETRAHEDRON LETTERS
Volume 56, Issue 30, Pages 4509-4511

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.05.117

Keywords

Bisnortriterpenoid; Biological activity; Synthesis; Vinylogous Mukaiyama aldol; Stereocontrol

Funding

  1. National Natural Science Foundation of China [21172096, 21472075]
  2. Fundamental Research Funds for the Central Universities [lzu-jbky-2014-59]
  3. '111' Project of MoE

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The first synthesis of 6,5,5,5-tetracyclic moiety related with promising anti-HIV activity in rubriflordilactone B has been efficiently achieved. Our strategy started from cheap materials, and features the utilization of radical 1,5-H abstraction/cyclization and vinylogous Mukaiyama aldol reaction, which successfully established the array of five continuous stereogenic carbon centers in the target. (C) 2015 Elsevier Ltd. All rights reserved.

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