Combined C-H activation/cope rearrangement as a strategic reaction in organic synthesis: Total synthesis of (-)-colombiasin A and (-)-elisapterosin B

  • Davies H
  • Dai X
  • Long M
  • 47


    Mendeley users who have this article in their library.
  • 131


    Citations of this article.


The total synthesis of (-)-colombiasin A (2) and (-)-elisapterosin B (3) has been achieved. The key step is a C-H functionalization process, the combined C-H activation/Cope rearrangement, between methyl (E)-2-diazo-3-pentenoate and 1-methyl-1,2-dihydronaphthalenes. When the reaction is catalyzed by dirhodium tetrakis((R)-(N-dodecylbenzenesulfonyl)prolinate), Rh(2)(R-DOSP)(4), an enantiomer differentiation step occurs where one enantiomer of the dihydronaphthalene undergoes the combined C-H activation/Cope rearrangement while the other undergoes cyclopropanation. This sequence controls the three key stereocenters in the natural products such that the remainder of the synthesis is feasible using standard chemistry.

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document


  • Huw M.L. Davies

  • Xing Dai

  • Matthew S. Long

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free