Acid-Promoted Cascade Cyclization to Produce 2-(4′-Alkoxyaryl)-3,4-Fused Tricyclic Dihydrobenzopyrans via a Vinylidene para-Quinone Methide Intermediate - UTU Research Portal

A1 Refereed original research article in a scientific journal

Acid-Promoted Cascade Cyclization to Produce 2-(4′-Alkoxyaryl)-3,4-Fused Tricyclic Dihydrobenzopyrans via a Vinylidene para-Quinone Methide Intermediate

Authors: Dongil Choi, Naoki Shiga, Robert Franzén, Tetsuhiro Nemoto

Publisher: Wiley-VCH Verlag

Publication year: 2018

Journal: European Journal of Organic Chemistry

Journal name in source: European Journal of Organic Chemistry

Volume: 2018

Issue: 15

First page : 1785

Last page: 1788

Number of pages: 4

ISSN: 1434-193X

DOI: https://doi.org/10.1002/ejoc.201800013

Abstract

We developed a novel method for synthesizing 2‐(4‐hydroxyaryl)‐3,4‐fused tricyclic
dihydrobenzopyrans with 2,3‐syn and 3,4‐syn motif based on the acid‐promoted cascade cyclization via vinylidene para‐quinone methide intermediates. Using easily prepared linear substrates, TFA‐promoted
cascade cyclization proceeded in the presence of triethylsilane, affording a series
of five to seven‐membered ring‐fused dihydrobenzopyran derivatives in moderate to
excellent yield in a highly diastereoselective manner. The developed method provided
new access to potent and selective ERβ agonists.