Synthesis 2023; 55(01): 90-106
Building Chemical Probes Based on the Natural Products YM-254890 and FR900359: Advances toward Scalability
Matthew R. Medcalf
a
Department of Chemistry, Washington University, St. Louis, MO, USA
,
Ruby L. Krueger
a
Department of Chemistry, Washington University, St. Louis, MO, USA
,
Zach T. Medcalf
a
Department of Chemistry, Washington University, St. Louis, MO, USA
,
Peter A. Rosston
a
Department of Chemistry, Washington University, St. Louis, MO, USA
,
Yu Zhu
a
Department of Chemistry, Washington University, St. Louis, MO, USA
,
Kevin M. Kaltenbronn
b
Department of Cell Biology and Physiology, Washington University School of Medicine, St. Louis, MO 63110, USA
,
Kendall J. Blumer∗
b
Department of Cell Biology and Physiology, Washington University School of Medicine, St. Louis, MO 63110, USA
,
Kevin D. Moeller∗
a
Department of Chemistry, Washington University, St. Louis, MO, USA
› Author Affiliations We thank the National Institutes of Health (2R01GM124093) for their generous support of our work.
Abstract
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.
Key words
YM-254890 -
FR900359 -
analogs -
scalable synthesis
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-1873-6891.
Supporting Information
Publication History
Received: 25 April 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
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