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Ring-closing metathesis in flavonoid synthesis, part 2: neoflav-3-enes.

Authors :
Pieterse, Tanya
Marais, Charlene
Bezuidenhoudt, Barend C. B.
Source :
ARKIVOC: Online Journal of Organic Chemistry. 2022, Vol. 2022, p217-231. 15p.
Publication Year :
2022

Abstract

A series of neoflav-3-enes with a variety of natural substitution patterns was prepared from 1-(allyloxy)-2-[1-(aryl)vinyl]benzenes by Grubbs second generation (GII) catalyst-promoted ring-closing metathesis (67 - 99% yield). The 1-(allyloxy)-2-[1-(phenyl)vinyl]benzene substrates were accessible in yields of 52 - 94% from the corresponding 2-(allyloxy)acetophenones via a Grignard reaction and Lewis acid-promoted dehydration, either in a one pot process in the presence of Al(OTf)3 or in consecutive steps with CuSO4 as dehydrating agent. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
15517004
Volume :
2022
Database :
Academic Search Index
Journal :
ARKIVOC: Online Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
161149214
Full Text :
https://doi.org/10.24820/ark.5550190.p011.759