170591-45-4Relevant articles and documents
First total synthesis of oteromycin utilizing one-pot four-step cascade reaction strategy
Uchiro, Hiromi,Shionozaki, Nobuhiro,Tanaka, Ryo,Kitano, Hiroyuki,Iwamura, Naoki,Makino, Kimiko
, p. 506 - 511 (2013/02/23)
The first total synthesis of oteromycin was investigated. Our previously reported convergent strategy for the synthesis of α-acyl-γ-hydroxy- γ-lactams was first applied for the total synthesis, however, the final deprotection of the methoxyaminal moiety could not be achieved since an unexpected intramolecular Diels-Alder (IMDA) reaction occurred. Therefore, a novel one-pot four-step cascade reaction starting from α-selenolactam was investigated. The efficient synthetic strategy was successfully developed to afford the desired oteromycin, and its complete structure elucidation including the stereochemistry at C24 position was also accomplished.
