Accessing Highly Oxidized Imidazolidinone Cores via a Curtius Rearrangement: Total Synthesis of Colensolide A

Org Lett. 2023 May 26;25(20):3698-3701. doi: 10.1021/acs.orglett.3c01139. Epub 2023 May 15.

Abstract

The hydroxytetrahydropyrrolo-imidazolidinone (HTHP-I) core present in colensolide A is a synthetically intriguing scaffold as a result of its high heteroatom/carbon ratio and perceived instability. The similarity of this core to other potent biological scaffolds has led us to develop a synthetic route utilizing isocyanate chemistry to access this core and complete the first total synthesis of colensolide A.