@article{0edcfecceb7e4369988862c2d6757ceb,
title = "Approach to Fully Substituted Cyclic Nitrones from N-Hydroxylactam Derivatives: Development and Application to the Total Synthesis of Cylindricine C",
abstract = "An approach to cyclic nitrones from N-hydroxylactam derivatives is documented. The nucleophilic addition of an organolithium reagent to an N-OSEM [SEM=2-(trimethylsilyl)ethoxymethyl] lactam forms a five-membered chelated intermediate, which undergoes both elimination and deprotection to give a fully substituted nitrone in a one-pot process. When combined with the N-oxidation of easily available chiral lactams, this method becomes especially useful for the quick synthesis of chiral nitrones in enantio-pure form, enabling the concise total synthesis of cylindricine C.",
keywords = "amides, nitrones, nucleophilic addition, synthetic methods, total synthesis",
author = "Shobu Hiraoka and Tsutomu Matsumoto and Koki Matsuzaka and Takaaki Sato and Noritaka Chida",
note = "Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (C) from MEXT (18K05127), the Tobe Maki foundation, and JGC-S Scholarship Foundation. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2019",
month = mar,
day = "22",
doi = "10.1002/anie.201901049",
language = "English",
volume = "58",
pages = "4381--4385",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "13",
}