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Divergent synthesis of complex diterpenes through a hybrid oxidative approach.

ABSTRACT: Polycyclic diterpenes exhibit many important biological activities, but de novo synthetic access to these molecules is highly challenging because of their structural complexity. Semisynthetic access has also been limited by the lack of chemical tools for scaffold modifications. We report a chemoenzymatic platform to access highly oxidized diterpenes by a hybrid oxidative approach that strategically combines chemical and enzymatic oxidation methods. This approach allows for selective oxidations of previously inaccessible sites on the parent carbocycles and enables abiotic skeletal rearrangements to additional underlying architectures. We synthesized a total of nine complex natural products with rich oxygenation patterns and skeletal diversity in 10 steps or less from ent-steviol.

SUBMITTER: Zhang X

PROVIDER: S-EPMC7569743 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Divergent synthesis of complex diterpenes through a hybrid oxidative approach.

Zhang Xiao X King-Smith Emma E Dong Liao-Bin LB Yang Li-Cheng LC Rudolf Jeffrey D JD Shen Ben B Renata Hans H

Science (New York, N.Y.) 20200801 6505

Polycyclic diterpenes exhibit many important biological activities, but de novo synthetic access to these molecules is highly challenging because of their structural complexity. Semisynthetic access has also been limited by the lack of chemical tools for scaffold modifications. We report a chemoenzymatic platform to access highly oxidized diterpenes by a hybrid oxidative approach that strategically combines chemical and enzymatic oxidation methods. This approach allows for selective oxidations o ...[more]

PMID: 32792393

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