Subscribe to RSS
DOI: 10.1055/s-0033-1340352
Synthesis of (+)-N-Methylwelwitindolinone D Isonitrile
Publication History
Publication Date:
13 December 2013 (online)
Key words
welwitindolinone D - isotope effect - nitrene insertion - C–H functionalization - aerobic oxidationSignificance
The welwitindolinones display interesting biological properties such as antifungal activity and microtubule depolymerization in human carcinoma cells. The challenging architecture of the target compound features an oxidized bicyclo[4.3.1]decane motif. The additional tetrahydrofuran ring was efficiently introduced by a double functionalization using air.
#
Comment
A was converted into deuterium-containing indolinone C. As described earlier by the authors, exploitation of the isotope effect during nitrene insertion afforded E in good yield. Oxidation to F was affected using tetra-n-butylammonium fluoride (TBAF) and air. Since hydrolysis of F led to decomposition, H was prepared by a reduction–hydrolysis–oxidation sequence. Formylation and dehydration yielded the target.
#
#