EDC/DMAP-mediated direct condensation of dicarboxylic acids and diols: A concise synthesis of extra large polyether macrocyclic lactones and their X-ray structures. Issue 51 (21st December 2016)

• Record Type: Journal Article
• Authors: Naveen, ; Babu, Srinivasarao Arulananda
• Is Part Of: Tetrahedron letters. Volume 57:Issue 51(2016)
• Page Start: 5801
• Page End: 5807
• Publication Date: 2016-12-21
• Subjects: Dicarboxylic acids -- Lactonization -- EDC/DMAP -- Macrocyclic lactones -- Polyether macrocycles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.11.046
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Direct condensation reactions of dicarboxylic acids with diols mediated by EDC/DMAP. Synthesis of new classes of 18-48 membered, small and extra-large polyether macrocyclic lactones. Macrocyclic lactone synthesis without template under relatively simple reaction conditions. Macrocyclization/Macrolactonization using simple starting materials. Abstract: We report the EDC/DMAP-mediated direct condensation reactions of dicarboxylic acids with diols and synthesis of new classes of 18-48-membered, small and extra-large polyether macrocyclic lactones. The methodology was executed by using various dicarboxylic acids linked via aliphatic, polyether and aromatic linkers and different diols (e.g., ( Z )-but-2-ene-1, 4-diol, but-2-yne-1, 4-diol, 2, 2′-thiobis(ethan-1-ol), 2, 2′-(benzylazanediyl)bis(ethan-1-ol), 2, 2′-oxybis(ethan-1-ol)). The condensation reactions of dicarboxylic acids with diols afforded 1:1 (18-24-membered) and 2:2 (36–48-membered) polyether macrocyclic lactones. The synthesis of small and extra-large polyether macrocyclic lactones was accomplished without using a template and relatively simple reaction conditions. All the reported macrocyclic lactones were separated by column chromatography and characterized by 1 H, 13 C NMR and HRMS analyses. The solid state (X-ray) structures of representative polyether macrocyclic lactones were also reported.