Total Synthesis and Late‐Stage C−H Oxidations of ent‐Trachylobane Natural Products
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ABSTRACT:
SUBMITTER: Wein L
PROVIDER: S-EPMC10947344 | biostudies-literature | 2021 Nov
REPOSITORIES: biostudies-literature
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Project description: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.
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