A new method for the polymer-supported synthesis of cyclic oligoesters for potential applications in macrocyclic lactone synthesis and combinatorial chemistry

Polymer-supported syntheses of oxo-crown ethers and derivatives containing α-amino-acid residues

“…The use of these new hydroxy-esters is of interest as the cyclic oligomers produced are oxo-crown ethers, or their derivatives, and they are expected to have interesting recognition properties [22,23]. Moreover, they are expected to be more soluble in polar solvents than their hydrocarbon chain counterparts [10,11]. Thus, for potential recognition purposes the present type of macrocycles are more interesting than those prepared previously by this PS method.…”

“…Cyclo-oligomerization is then achieved by treating the supported hydroxy-ester with a catalytic amount of di-n-butyltin oxide. In this process ester links are formed which can create linear oligomers on the beads and/or which can cause cyclizations that result in the detachment of the oligoesters from the beads [10]. Linear species formed remain bound to the beads: only cyclic species are released into solution.…”

“…In an earlier paper we described simple polymer-supported (PS) syntheses of various macrocyclic esters [10].…”

“…Another attractive feature of the present method is that it lends itself to the synthesis of the required hydroxy-esters on the beads. Thus, PS hydroxy-esters 1 and 2 [10] and hydroxyacylpeptides 3 [11] have all been prepared on the beads and then cyclo-oligomerized.…”

The chemistry of the carbon–transition metal double and triple bond: annual survey covering the year 2002

“…65) [226], including carbohydrates [227]; (3) O-allylcarbohydrate derivatives (e.g. 66) and formation of macrocycle-bridged carbohydrates through RCM [228]; (4) gold nanoclusters [229]; and (5) polymer-supported 10-undecenoic acid derivatives [230].…”