4.5 Article

Total Syntheses of Cochliomycin B and Zeaenol

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 10, Pages 2092-2098

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301613

Keywords

Natural products; Total synthesis; Lactones; Coupling reactions; Metathesis

Funding

  1. National Basic Research Program of China [2012CB822101]
  2. National Innovative Drug Fundation [2012ZX09502001]
  3. National Natural Science Foundation of China (NSFC) (NSF of China) [21072217, 21232002]

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Divergent syntheses of two 14-membered resorcylic acid lactones (RALs), cochliomycin B (6) and zeaenol (22), have been accomplished. The key feature in our strategy was the facile construction of three contiguous stereogenic centers in the title molecules by using natural L-arabinose as the chiral template. The key reactions included Takai olefination, Suzuki cross coupling, transesterification, and a late-stage ring-closing metathesis (RCM).

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