Solid phase combinatorial synthesis of a library of macro-heterocycles and related acyclic compounds

M Ramaseshan; Y L Dory; P Deslongchamps

doi:10.1021/cc000030y

Solid phase combinatorial synthesis of a library of macro-heterocycles and related acyclic compounds

J Comb Chem. 2000 Nov-Dec;2(6):615-23. doi: 10.1021/cc000030y.

Authors

M Ramaseshan¹, Y L Dory, P Deslongchamps

Affiliation

¹ Département de Chimie, and NéoKimia Inc., Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Québec, Canada.

PMID: 11126291
DOI: 10.1021/cc000030y

Abstract

A solid phase synthesis of macrolactones from three building blocks and in eight steps is described. The synthesis which is carried out on the DHP resin includes Mitsunobu and DIC couplings. The macrocyclization occurs by SN2 displacement of an allylic chloride by a malonate anion. The synthetic methodology is suitable for the synthesis of arrays of macrocycles as well as linear compounds.