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 - 2008 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Total synthesis of (-)-agelastatin A. / Yoshimitsu, Takehiko; Ino, Tatsunori; Tanaka, Tetsuaki.
In: Organic Letters, Vol. 10, No. 23, 2008, p. 5457-5460.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total synthesis of (-)-agelastatin A
AU - Yoshimitsu, Takehiko
AU - Ino, Tatsunori
AU - Tanaka, Tetsuaki
PY - 2008
Y1 - 2008
N2 - (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.
AB - (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.
UR - http://www.scopus.com/inward/record.url?scp=61349122654&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=61349122654&partnerID=8YFLogxK
U2 - 10.1021/ol802225g
DO - 10.1021/ol802225g
M3 - Article
C2 - 19006318
AN - SCOPUS:61349122654
VL - 10
SP - 5457
EP - 5460
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 23
ER -