4.6 Article

Toward the Total Synthesis of Haliclonin A: Construction of a Tricyclic Substructure

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 1, Pages 87-91

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201203203

Keywords

alkaloids; haliclonin A; palladium; ring-closing metathesis; total synthesis; transition metals

Funding

  1. NSF of China [20832005, 21072160]
  2. National Basic Research Program (973 Program) of China [2010CB833200]

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Three keys to success: A concise method for the construction of a tricyclic substructure (2) of haliclonin A (1) in racemic form is described (see figure). This synthesis features a new Pd-mediated chemoselective carbonyl-enone coupling reaction, an organocatalytic reaction, and a ring-closing metathesis reaction for the construction of the macrocyclic ring as key steps.

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