Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold

Viktoria A. Ikonnikova, Cristina Cheibas, Oscar Gayraud, Alexandra E. Bosnidou, Nicolas Casaretto, Gilles Frison and Bastien Nay

Beilstein J. Org. Chem. 2024, 20, 162–169. https://doi.org/10.3762/bjoc.20.15

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Scheme 3

Calculated using the Chemistry Development Kit 2.12

Property Name	Property Value
Molecular Formula	C₂₅H₃₂O₈
Molecular Weight	460.52 g/mol
Exact Mass	460.2097 Da
InChI	InChI=1S/C25H32O8/c1-6-32-23(27)25(24(28)33-7-2,15-17-11-9-8-10-12-17)16-19(26)22-20(30-4)13-18(29-3)14-21(22)31-5/h8-14,19,26H,6-7,15-16H2,1-5H3
InChIKey	JGAFFHSVZSPKDF-UHFFFAOYSA-N
SMILES	CCOC(=O)C(CC1=CC=CC=C1)(CC(C2=C(C=C(C=C2OC)OC)OC)O)C(=O)OCC
Number of Atoms	65
Number of H-Bond Acceptors	8
Number of H-Bond Donors	1
Atoms in the Largest π-System	9
XLogP	4.1

Operator	Resulting query
aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)