Total Syntheses of (–)-β- and (–)-γ-Naphthocyclinones

Keywords

(–)-β-naphthocyclinones - (–)-γ-naphthocyclinones - dimeric pyranonaphthoquinone - rhodium-mediated 1,4-addition - reductive cyclization - oxidative lactonization

Significance

Suzuki, Ohmori, Ando and co-workers report the first total syntheses of (–)-β- and (–)-γ-naphthocyclinones. Followed by series of sequential stereocontrolled steps to access the enantioselective synthesis of the unusual bicyclo[3.2.1]octadienone core, the authors completed the syntheses of the two dimeric pyranonaphthoquinones.

Comment

Two monomer fragments C and D were both synthesized from precursor B. Facile 1,4-addition mediated by non-racemic catalyst E gave naphthalene F. Functional group adjustments and oxidation generated G, which sequentially proceeded to reductive cyclization to yield H to ultimately access (–)-β-naphthocyclinone. Lastly, oxidative lactonization completed the synthesis of (–)-γ-naphthocyclinone.

Publication History

Article published online:
20 December 2024