Towards a Synthesis of Naphthalene Derived Natural Products

The dearomatization of 2‐naphthols represents a simple method for the construction of complex 3D structures from simple planar starting materials. We describe a cyclopropanation of 2‐naphthols that proceeds via cyclopropene ring‐opening using rhodium and acid catalysis under mild conditions. The vinyl cyclopropane molecules were formed with high chemoselectivity and scalability, which could be further functionalized at different sites. Both computational and experimental evidence were used to elucidate the reaction mechanism.

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Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring‐Opening

Baker

Ching

Hou

et al. 2022

Angewandte Chemie

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Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring‐Opening

et al. 2022

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Carbonyl Directed Regioselective Hydration of Alkynes under Ag‐Catalysis

Santhi

Baire

2017

ChemistrySelect

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A mild strategy for highly regioselective hydration of the alkynes (internal and terminal) has been developed employing intramolecular ketone as the directing group under Ag(I) catalysis. In this process both internal and terminal alkynes exhibited 100 % complementary reactivity i. e. 6‐endo‐dig vs. 5‐exo‐dig respectively, and provided two regio‐isomeric dicarbonyl products as exclusive products. This process found very broad scope for the ketones and alkynes. The 1,5‐diketones were efficiently transformed in to synthetically and pharmaceutically important naphthalene derivatives employing an intramolecular Aldol condensation.

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Towards a Synthesis of Naphthalene Derived Natural Products

Cited by 9 publications

References 11 publications

Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring‐Opening

Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring‐Opening

Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring‐Opening

Carbonyl Directed Regioselective Hydration of Alkynes under Ag‐Catalysis

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