Enantioselective Synthesis of a Tricyclic, sp³ -Rich Diazatetradecanedione: an Amino Acid-Based Natural Product-Like Scaffold.

ABSTRACT: 6-, 7-, and 8-membered rings are assembled from a linear precursor by successive cyclisation reactions to construct a tricyclic diazatricyclo[6.5.1.0^4, 9 ]-tetradecanedione scaffold. Advanced building blocks based on d-aspartic acid and l-pyroglutamic acid were combined by a sp³ -sp² Negishi coupling. A carbamate-guided syn-diastereoselective epoxidation followed by an intramolecular epoxide opening allowed the construction of the piperidine ring. An efficient one-pot hydroxyl-group protection twofold deprotection reaction prepared the ground for the cyclisation to the bicycle. A final deprotection of the orthogonal protecting groups and lactamisation led to the novel, sp³ -rich tricycle. The final compound is a substrate mimic of peptidyl-prolyl

SUBMITTER: Bischoff M 

PROVIDER: S-EPMC7187416 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature