Abstract
The second-generation approach to (-)-agelastatin A has been established. The present strategy features the FeBr2-mediated radical cyclization of 2-cyclopentenyloxycarbonyl azide that allows for the stereoselective installation of a cis-vicinal aminobromo functionality suitable for producing the BCD-ring system of agelastatin A. The aminobromination method streamlines access to oxazolidinone, a key intermediate in the previously reported synthesis, thereby culminating in the new total synthesis of (-)-agelastatin A.
| Original language | English |
|---|---|
| Pages (from-to) | 3402-3405 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 11 |
| Issue number | 15 |
| DOIs | |
| Publication status | Published - Aug 6 2009 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Yoshimitsu, T., Ino, T., Futamura, N., Kamon, T., & Tanaka, T. (2009). Total synthesis of the β-caten in inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination. Organic Letters, 11(15), 3402-3405. https://doi.org/10.1021/ol9012684