Synfacts 2014; 10(9): 0893
DOI: 10.1055/s-0034-1378570
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the Antifungal Agent ASP9726

Rezensent(en):
Philip Kocienski
Yoshida S * et al. Astellas Pharma Inc., Ibaraki and Tokyo, Japan
A Challenging Synthesis of the Highly Functionalized Echinocandin ASP9726: A Successor of Micafungin.

Org. Process Res. Dev. 2014;
18: 725-738
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Publikationsverlauf

Publikationsdatum:
18. August 2014 (online)

 

Significance

An 11-step synthesis of the antifungal agent ASP9726 (13.8% overall) from the fermentation product FR901379 is described that is remarkable for the highly chemoselective transformations on functionally dense substrates.


Comment

The closing stages of the synthesis feature the reductive amination of primary amine C with dihydroxyacetone using 2-picoline·borane and reductive amination of core peptide G with side chain H using t-BuNH2·borane complex.