Total Synthesis and Late-Stage C-H Oxidations of ent-Trachylobane Natural Products.

ABSTRACT: Herein, we present our studies to construct seven ent-trachylobane diterpenoids by employing a bioinspired two-phase synthetic strategy. The first phase provided enantioselective and scalable access to five ent-trachylobanes, of which methyl ent-trachyloban-19-oate was produced on a 300 mg scale. During the second phase, chemical C-H oxidation methods were employed to enable selective conversion to two naturally occurring higher functionalized ent-trachylobanes. The formation of regioisomeric analogs, which are currently inaccessible via enzymatic methods, reveals the potential as well as limitations of established chemical C-H oxidation protocols for complex molecule synthesis.

SUBMITTER: Wein LA 

PROVIDER: S-EPMC7612322 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature