Issue 16, 2023

Construction of cyclopenta[b]dihydronaphthofurans via TsOH-catalyzed consecutive biscyclization of dithioallylic alcohols and 1-styrylnaphthols

Abstract

An efficient TsOH-catalyzed consecutive biscyclization cascade reaction of dithioallylic alcohols with 1-styrylnaphthols is demonstrated for the concise construction of pharmaceutically important cyclopenta[b]dihydrobenzofuran scaffolds. This process involved an acid-catalyzed (3+2) cycloaddition followed by an intramolecular nucleophilic addition, providing cyclopenta[b]dihydronaphthofurans bearing a tetra- or fully substituted cyclopentane core in good yields with exclusive diastereoselectivities (>20 : 1 d.r.).

Graphical abstract: Construction of cyclopenta[b]dihydronaphthofurans via TsOH-catalyzed consecutive biscyclization of dithioallylic alcohols and 1-styrylnaphthols

Supplementary files

Article information

Article type
Communication
Submitted
22 Nov 2022
Accepted
27 Jan 2023
First published
30 Jan 2023

Chem. Commun., 2023,59, 2275-2278

Construction of cyclopenta[b]dihydronaphthofurans via TsOH-catalyzed consecutive biscyclization of dithioallylic alcohols and 1-styrylnaphthols

H. Li, X. Wu, G. Zhan, X. Fu, J. Chen, X. He and B. Han, Chem. Commun., 2023, 59, 2275 DOI: 10.1039/D2CC06324G

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