Abstract
(Chemical Equation Presented) A new route to (-)-agelastatin A is reported. The requisite nitrogen functionalities of the agelastatin core have been installed by intramolecular aziridination of an azidoformate and subsequent regioselective azidation, leading to net trans-diamination of the double bond. The present synthesis also demonstrates two new protocols for the preparation of an imidazolidinone hemiaminal motif from an oxazolidinone intermediate which comprise sequential N-tert-butoxycarbonylation, urea formation, hydrolysis, and oxidative cyclization, and direct aminolysis and subsequent oxidative cyclization.
| Original language | English |
|---|---|
| Pages (from-to) | 5457-5460 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 10 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - Dec 1 2008 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Fingerprint Dive into the research topics of 'Total synthesis of (-)-agelastatin A'. Together they form a unique fingerprint.
Cite this
Yoshimitsu, T., Ino, T., & Tanaka, T. (2008). Total synthesis of (-)-agelastatin A. Organic Letters, 10(23), 5457-5460. https://doi.org/10.1021/ol802225g