1009736-88-2Relevant academic research and scientific papers
C-H Functionalization of N-Methylated Amino Acids and Peptides as Tool in Natural Product Synthesis: Synthesis of Abyssenine A and Mucronine e
Kinsinger, Thorsten,Kazmaier, Uli
, p. 7726 - 7730 (2018)
N-Methylated amino acids and peptides with an 8-aminoquinoline (AQ) directing group can be subjected to stereoselective Pd-catalyzed β-functionalizations. The best results are obtained with aryl iodides, but alkyl and alkenyl side chains can also be introduced. The AQ protecting group can easily be removed, providing the free carboxylic acid, which can be used directly in peptide couplings. This protocol was used successfully as a key step in the synthesis of the cyclopeptide alkaloids abyssenine A and mucronine E.
Eight-step total synthesis of the cyclopeptide alkaloid mucronine E
Toumi, Mathieu,Couty, Fran?ois,Evano, Gwilherm
, p. 29 - 32 (2008/09/21)
An eight-step total synthesis of the 15-membered ring cyclopeptide alkaloid mucronine E is reported. Key steps include the formation of the highly substituted aromatic core using an asymmetric hydrogenation-Vilsmeier formylation sequence. Central to our approach was a macroamidation protocol using a copper-catalyzed coupling reaction to install the enamide with a concomitant straightforward macrocyclization. This synthesis also allowed for the assignment of both relative and absolute configurations of mucronine E. Georg Thieme Verlag Stuttgart.
