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Total Synthesis of Cladosins B and C
Keith P Reber1, James Mease1, Justin Kim1
1Department of Chemistry, Towson University, Towson, Maryland 21252, United States.
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.
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