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 |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Total synthesis of the β-caten in inhibitor, (-)-agelastatin A : A second-generation approach based on radical aminobromination. / Yoshimitsu, Takehiko; Ino, Tatsunori; Futamura, Naoyuki; Kamon, Takuma; Tanaka, Tetsuaki.
In: Organic Letters, Vol. 11, No. 15, 06.08.2009, p. 3402-3405.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total synthesis of the β-caten in inhibitor, (-)-agelastatin A
T2 - A second-generation approach based on radical aminobromination
AU - Yoshimitsu, Takehiko
AU - Ino, Tatsunori
AU - Futamura, Naoyuki
AU - Kamon, Takuma
AU - Tanaka, Tetsuaki
PY - 2009/8/6
Y1 - 2009/8/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=68149141337&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=68149141337&partnerID=8YFLogxK
U2 - 10.1021/ol9012684
DO - 10.1021/ol9012684
M3 - Article
C2 - 19588910
AN - SCOPUS:68149141337
VL - 11
SP - 3402
EP - 3405
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 15
ER -