Enantioselective total synthesis of atpenin A5.

Masaki Ohtawa, Satoru Ogihara, Kouhei Sugiyama, Kazuro Shiomi, Yoshihiro Harigaya, Tohru Nagamitsu, Satoshi Omura

School of Pharmacy, Kitasato University, Shirokane, Minato-ku, Tokyo, Japan.

The Journal of antibiotics 2009 Jun

filter terms:

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.

Citation

Masaki Ohtawa, Satoru Ogihara, Kouhei Sugiyama, Kazuro Shiomi, Yoshihiro Harigaya, Tohru Nagamitsu, Satoshi Omura. Enantioselective total synthesis of atpenin A5. The Journal of antibiotics. 2009 Jun;62(6):289-94