Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 13, Pages 4381-4385Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201901049
Keywords
amides; nitrones; nucleophilic addition; synthetic methods; total synthesis
Categories
Funding
- MEXT [18K05127]
- JGC-S Scholarship Foundation
- Tobe Maki foundation
- Grants-in-Aid for Scientific Research [18K05127] Funding Source: KAKEN
Ask authors/readers for more resources
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 cylindricineC.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available