A Malaprade cleavage, a McMurry ring closure and an intramolecular aldol contraction of maslinic acid’s ring A

Sophie Hoenke; Immo Serbian; René Csuk

doi:10.1016/j.rechem.2022.100547

Results in Chemistry (Jan 2022)

A Malaprade cleavage, a McMurry ring closure and an intramolecular aldol contraction of maslinic acid’s ring A

Sophie Hoenke,
Immo Serbian,
René Csuk

Affiliations

Sophie Hoenke: Martin-Luther University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str.2, D-06120 Halle (Saale), Germany
Immo Serbian: Martin-Luther University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str.2, D-06120 Halle (Saale), Germany
René Csuk: Corresponding author.; Martin-Luther University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str.2, D-06120 Halle (Saale), Germany

DOI: https://doi.org/10.1016/j.rechem.2022.100547
Journal volume & issue: Vol. 4
p. 100547

Abstract

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A silica gel supported Malaprade cleavage of methyl maslinoate (→3) followed by a titanium-on-graphite supported McMurry coupling was established to access a 2,12-terpenoid. The microwaves supported aldol reaction of dialdehyde 3 gave ring contracted 5. While parent maslinic acid is of minor cytotoxicity, improved cytotoxicity was observed in SRB assays for 3 while ring contracted compound 5 was most cytotoxic for MCF-7 breast adenocarcinoma cells holding a low EC50 = 3.1 μM.

Published in Results in Chemistry

ISSN: 2211-7156 (Online)
Publisher: Elsevier
Country of publisher: Netherlands
LCC subjects: Science: Chemistry
Website: https://www.journals.elsevier.com/results-in-chemistry/

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