Total Synthesis of Cladosins B and C
- 5 August 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (17), 11571-11578
- https://doi.org/10.1021/acs.joc.0c01605
Abstract
A convergent synthetic route to the fungal metabolites cladosins B and C has been developed, affording these natural products in 29% and 27% overall yield, respectively. The cladosins are rare examples of hybrid polyketides featuring a 3-enamine tetramic acid group derived from L-valine. Key steps in this modular six-step sequence include a DMAP-mediated O- to C-acyl rearrangement to unite the side chains with the tetramic acid core and subsequent amine incorporation using either ammonium acetate or HMDS.Keywords
Funding Information
- Jess and Mildred Fisher College of Science and Mathematics
- Towson University
- American Chemical Society
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