Total synthesis of the beta-catenin inhibitor, (-)-agelastatin A: a second-generation approach based on radical aminobromination.
The second-generation approach to (-)-agelastatin A has been established. The present strategy features the FeBr(2)-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.
Yoshimitsu
Takehiko
T
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. yoshimit@phs.osaka-u.ac.jp
Ino
Tatsunori
T
Futamura
Naoyuki
N
Kamon
Takuma
T
Tanaka
Tetsuaki
T
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D058085:Iron Compounds / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D051176:beta Catenin / Q000037:antagonists & inhibitors*
D000470:Alkaloids; D000970:Antineoplastic Agents; D058085:Iron Compounds; D023303:Oxazolidinones; C464968:agelastatin A; D051176:beta Catenin