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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

Contributor(s):
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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Publication History

Publication Date:
18 August 2014 (online)

 
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Key words

ASP9726 - reductive amination - amide dehydration - enzymatic hydrolysis of amides

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.


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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.


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