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A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

preprint
submitted on 01.06.2018 and posted on 04.06.2018 by Christian R. Zwick III, Hans Renata
We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

Funding

The Scripps Research Institute, The Farris Foundation

History

Email Address of Submitting Author

hrenata@scripps.edu

Email Address(es) for Other Author(s)

czwick@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2468-2328

Declaration of Conflict of Interest

No conflict of interest

Exports