An enantiospecific total synthesis of the pyrrole-imidazole natural product cyclooroidin from histidine is described. The key N1-C9 bond is constructed through an intramolecular SN2-type of reaction of a chloro ester. Subsequent imidazole azidation at the 2-position, pyrrole bromination, azide reduction, and deprotection leads to the completion of the synthesis.
An enantiospecific total synthesis of the pyrrole-imidazolenatural product n class="Chemical">cyclooroidin from histidine is described. The key N1-C9 bond is constructed through an intramolecular SN2-type of reaction of a chloro ester. Subsequent imidazole azidation at the 2-position, pyrrole bromination, azide reduction, and deprotection leads to the completion of the synthesis.
Authors: Yong-Gang Wang; Brandon I Morinaka; Jeremy Chris P Reyes; Jeremy J Wolff; Daniel Romo; Tadeusz F Molinski Journal: J Nat Prod Date: 2010-03-26 Impact factor: 4.050
Authors: Apsara K Herath; Manoj R Bhandari; Delphine Gout; Muhammed Yousufuddin; Carl J Lovely Journal: Tetrahedron Lett Date: 2017-08-24 Impact factor: 2.415