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Synfacts 2014; 10(1): 0011
DOI: 10.1055/s-0033-1340352
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-N-Methylwelwitindolinone D Isonitrile

Contributor(s):
Erick M. Carreira
,
Matthias Westphal
Styduhar ED, Huters AD, Weires NA, Garg NK * University of California, Los Angeles, USA
Enantiospecific Total Synthesis of N-Methylwelwitindolinone D Isonitrile.

Angew. Chem. Int. Ed. 2013;
52: 12422-12425
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

welwitindolinone D - isotope effect - nitrene insertion - C–H functionalization - aerobic oxidation

Significance

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.


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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.


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