Total Synthesis of Cladosins B and C

• DOI: 10.1021/acs.joc.0c01605
• Publication Date: 2020-08-05T08:59:57Z
• Authors: Keith P. Reber; James Mease; Justin Kim
• Keywords: 01 natural sciences; 0104 chemical sciences

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.