Enantioselective total synthesis of atpenin A5.
Enantioselective total synthesis of atpenin A5, a potent mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor, has been achieved by a convergent approach through a coupling reaction between 5-iodo-2,3,4,6-tetraalkoxypyridine and a side-chain aldehyde. The two key segments were synthesized through ortho-metalation/boronation with (MeO)3B/oxidation with mCPBA, ortho-iodination, halogen dance reaction, Sharpless epoxidation and regioselective epoxide-opening reaction. This synthetic study resulted in the revision of the earlier reported 1H-NMR data of the natural atpenin A5 and the confirmation of the stereochemical assignment.
School of Pharmacy, Kitasato University, Shirokane, Minato-ku, Tokyo, Japan.
Masaki
M
Ohtawa
Satoru
S
Ogihara
Kouhei
K
Sugiyama
Kazuro
K
Shiomi
Yoshihiro
Y
Harigaya
Tohru
T
Nagamitsu
Satoshi
S
Omura
D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011728:Pyridones / Q000138:chemical synthesis*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D007202:Indicators and Reagents; D011728:Pyridones; C058278:atpenin A5