1. Synthesis of alpha-onoceradiene-like terpene dimers by intermolecular metathesis processes
María C de la Torre, Antonio M Deometrio, Elsa Alvaro, Isabel García, Miguel A Sierra Org Lett. 2006 Feb 16;8(4):593-6. doi: 10.1021/ol052680m.
[reaction: see text] New alpha-onoceradiene analogues having a terpene homodimer skeleton are accessible from Weinreb's amide 2 derived from commercial (R)-(+)-sclareolide using an intermolecular metathesis reaction as the key step to build the linker joining both terpene moieties.
2. Pd(OAc)2/DABCO as an efficient and phosphine-free catalytic system for the synthesis of single and double Weinreb amides by the aminocarbonylation of aryl iodides
Sandip T Gadge, Bhalchandra M Bhanage Org Biomol Chem. 2014 Aug 14;12(30):5727-32. doi: 10.1039/c4ob00729h. Epub 2014 Jun 26.
This work reports a mild, stable and efficient Pd(OAc)2/DABCO catalysed protocol for the synthesis of single and double Weinreb amides. Double Weinreb amides, having 1,4-phenylene- and biphenylene-linkers - important backbones for the synthesis of biologically active symmetrical resorcylate oligomer units - were synthesized by the double carbonylation of aryl diiodides. Notably, the reaction does not require any expensive or air/moisture sensitive phosphine ligands. DABCO was found to be an inexpensive and stable ligand for the Pd(OAc)2 catalysed carbonylation of aryl iodides under an atmospheric pressure of carbon monoxide, and offered excellent yields of the single and double Weinreb amides.
3. Peptide Weinreb amide derivatives as thioester precursors for native chemical ligation
Chang Rao, Chuan-Fa Liu Org Biomol Chem. 2017 Mar 28;15(12):2491-2496. doi: 10.1039/c7ob00103g. Epub 2017 Feb 7.
Peptide Weinreb amide derivatives with an N-substituted mercaptoethyl group are designed as thioester precursors for native chemical ligation. We show that these amides undergo rapid ligation with a cysteinyl peptide under normal NCL conditions to form various Xaa-Cys peptide bonds, including the difficult Val-Cys junction. Facile synthesis of the Weinreb amide linkers allows easy access to this new type of peptide thioester precursor by standard Fmoc solid phase synthesis.
