Macrocyclization of 2-(5-(2-hydroxyethyl)furan-2-yl)acetic acid model compounds of nonactic acid
Author(s)
Date issued
2009
In
Monatsh. Chem.
Vol
3
No
140
From page
349
To page
354
Subjects
Natural products (nonactin analogs prepn. of macrocyclic compds. by cyclization of (hydroxyalkyl)furanacetic acid derivs. with dichlorobenzoyl chloride) Cyclization Debenzylation Hydrogenolysis Macrocyclization (prepn. of macrocyclic compds. by cyclization of (hydroxyalkyl)furanacetic acid derivs. with dichlorobenzoyl chloride) Macrocyclic compounds Role: SPN (Synthetic preparation) PREP (Preparation) (prepn. of macrocyclic compds. by cyclization of (hydroxyalkyl)furanacetic acid derivs. with dichlorobenzoyl chloride) macrocyclization nonactic acid hydroxyethyl furanacetic acid prepn macrocyclization natural product analog nonactin prepn macrocyclization
Abstract
A method for the synthesis of macrocyclic compds. is reported here. The macrocyclization of (hydroxyethyl)furanacetic acid and of dehydrogenated model compds. of nonactic acid was investigated to develop a facile synthesis of nonactin analogs. By applying the Yamaguchi macrocyclization to ?-hydroxy carboxylic acids [i.e., 5-(2-hydroxyethyl)-2-furanacetic acid and 5-(2-hydroxyethyl)-?-(phenylmethyl)-2-furanacetic acid], it was possible to isolate a mixt. of di-, tri-, tetra- and pentameric macrocyclic compds. [on SciFinder(R)]
Publication type
journal article