Abstract
Pyrogallol and its derivatives are biologically active compounds, and pyrogallol also forms the basis of an increasingly important tetrameric supramolecular scaffold. Pyrogallol[4]arenes are tetrameric macrocycles that form from 1,2,3-trihydroxybenzene and aldehydes under acidic conditions. Pyrogallol was treated with two equivalents of pivaloyl chloride to form pyrogallyl dipivaloate. A mixture of regioisomers was invariably obtained and a rapid equilibrium was observed between the 1,2- and 1,3-diesters in polar solvents. A pure sample of solid pyrogallyl 1,2-dipivaloate was isolated and its crystal structure was obtained. The pure compound was shown to rearrange to mixtures similar to those isolated initially.
Original language | English (US) |
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Pages (from-to) | 333-336 |
Number of pages | 4 |
Journal | Natural Product Communications |
Volume | 7 |
Issue number | 3 |
DOIs | |
State | Published - Mar 2012 |
Externally published | Yes |
Keywords
- Acyl migration
- Pivalic acid
- Protecting group
- Pyrogallol
- Pyrogallol[4]arene
- Solvent effect
ASJC Scopus subject areas
- Pharmacology
- Plant Science
- Drug Discovery
- Complementary and alternative medicine