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Total Synthesis of Chaetoglobin A via Catalytic, Atroposelective Oxidative Phenol Coupling.

ABSTRACT: The first total synthesis of chaetoglobin A (1), which features a chiral axis between two identical highly oxygenated bicyclic cores, was successfully completed in 12 steps from 2,6-dimethoxytoluene. Vanadium-catalyzed oxidative phenol coupling, as a key step, enabled generation of the axial chirality.

SUBMITTER: Kang H

PROVIDER: S-EPMC6174078 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Total Synthesis of Chaetoglobin A via Catalytic, Atroposelective Oxidative Phenol Coupling.

Kang Houng H Torruellas Carilyn C Liu Jinchu J Kozlowski Marisa C MC

Organic letters 20180912 18

The first total synthesis of chaetoglobin A (1), which features a chiral axis between two identical highly oxygenated bicyclic cores, was successfully completed in 12 steps from 2,6-dimethoxytoluene. Vanadium-catalyzed oxidative phenol coupling, as a key step, enabled generation of the axial chirality. ...[more]

PMID: 30207731

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