Building Chemical Probes Based on the Natural Products YM-254890 and FR900359: Advances toward Scalability

The biological activity of natural products YM-254890 (YM) and FR900359 (FR) has led to significant interest in both their synthesis and the construction of more simplified analogs. While the simplified analogs lose much of the potency of the natural products, they are of interest in their own right...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 55; no. 1; pp. 90 - 106
Main Authors Medcalf, Matthew R., Krueger, Ruby L., Medcalf, Zach T., Rosston, Peter A., Zhu, Yu, Kaltenbronn, Kevin M., Blumer, Kendall J., Moeller, Kevin D.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.01.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PROTEIN
YM-254890
analogs
scalable synthesis
FR900359
INHIBITOR
CYCLIC DEPSIPEPTIDE
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Summary:The biological activity of natural products YM-254890 (YM) and FR900359 (FR) has led to significant interest in both their synthesis and the construction of more simplified analogs. While the simplified analogs lose much of the potency of the natural products, they are of interest in their own right, and their synthesis has revealed synthetic barriers to the family of molecules that need to be addressed if a scalable synthesis of YM and FR analogs is to be constructed. In the work described here, a synthetic route to simplified analogs of YM is examined and strategies for circumventing some of the challenges inherent to constructing the molecules are forwarded.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1873-6891