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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Figure 2

Calculated using the Chemistry Development Kit 2.12

Property Name	Property Value
Molecular Formula	C₂₂H₂₂O₈
Molecular Weight	414.41 g/mol
Exact Mass	414.1315 Da
InChI	InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1
InChIKey	YJGVMLPVUAXIQN-XVVDYKMHSA-N
SMILES	COC1=CC(=CC(=C1OC)OC)[C@@H]2C3=C(C=C4C(=C3)OCO4)[C@@H]([C@@]5([H])COC(=O)[C@@]52[H])O
Number of Atoms	52
Number of H-Bond Acceptors	8
Number of H-Bond Donors	1
Atoms in the Largest π-System	9
XLogP	0.7

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)