Synthesis of the Antifungal Agent ASP9726

Philip Kocienski

doi:10.1055/s-0034-1378570

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Synfacts 2014; 10(9): 0893
DOI: 10.1055/s-0034-1378570

Synthesis of Natural Products and Potential Drugs

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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Further Information

Publication History

Publication Date:
18 August 2014 (online)

Abstract
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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.

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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