11076-19-0Relevant articles and documents
Efficient Total Synthesis of Bongkrekic Acid and Apoptosis Inhibitory Activity of Its Analogues
Matsumoto, Kenji,Suyama, Masaki,Fujita, Satoshi,Moriwaki, Takuya,Sato, Yukiko,Aso, Yoshifumi,Muroshita, Satoshi,Matsuo, Hiroshi,Monda, Keishi,Okuda, Katsuhiro,Abe, Masato,Fukunaga, Hiroyuki,Kano, Arihiro,Shindo, Mitsuru
, p. 11590 - 11602 (2015/08/03)
Bongkrekic acid (BKA), isolated from the bacterium Burkholderia cocovenenans, is an inhibitor of adenine nucleotide translocator, which inhibits apoptosis, and is thus an important tool for the mechanistic investigation of apoptosis. An efficient total synthesis of BKA has been achieved by employing a three-component convergent strategy based on Kocienski-Julia olefination and Suzuki-Miyaura coupling. It is noteworthy that segment B has been prepared as a new doubly functionalized coupling partner, which contributes to shortening of the number of steps. Torquoselective olefination with an ynolate has also been applied for the efficient construction of an unsaturated ester. Furthermore, it is revealed that 1-methyl-2-azaadamantane N-oxyl is an excellent reagent for final oxidation to afford BKA in high yield. Based on the total synthesis, several BKA analogues were prepared for structure-activity relationship studies, which indicated that the carboxylic acid moieties were essential for the apoptosis inhibitory activity of BKA. More easily available BKA analogues with potent apoptosis inhibitory activity were also developed. Stripped BKA: The highly efficient second-generation total synthesis of bongkrekic acid (BKA), an apoptosis inhibitor, has been developed. The synthesis features a three-component convergent strategy based on a Kocienski-Julia olefination and Suzuki-Miyaura coupling. The structure-activity relationship (SAR) is also examined for the first time (see scheme).
Total synthesis of iso- and bongkrekic acids: Natural antibiotics displaying potent antiapoptotic properties
Francais, Antoine,Leyva-Perez, Antonio,Etxebarria-Jardi, Gorka,Pena, Javier,Ley, Steven V.
, p. 329 - 343 (2011/03/21)
For over five decades, owing to their antiapoptotic activities, bongkrekic and isobongkrekic acids have generated interest from the scientific community. Here, we disclose full details of our investigation into the synthesis of isobongkrekic acid, which culminated in its first preparation and features various palladium-catalysed cross-couplings and Takai olefination reactions. Access to bongkrekic acid is also reported by this route. These syntheses involve the preparation and use of new general building blocks which could find wider applications. Iso-bong: A versatile first synthesis of isobongkrekic acid (IBA) has been developed. Key steps include three different palladium cross-couplings and an asymmetric homopropargylation. In-depth synthetic studies reveal the challenges faced in generating the right geometry of each diene.
Total synthesis of the anti-apoptotic agents Iso- And bongkrekic acids
Francais, Antoine,Leyva, Antonio,Etxebarria-Jardi, Gorka,Ley, Steven V.
supporting information; experimental part, p. 340 - 343 (2010/03/25)
(Figure presented) The first convergent total synthesis of isobongkrekic acid is reported involving three different stereospecific palladium cross-couplings for the formation of the diene units. Access to bongkrekic acid by this route is also demonstrated. These syntheses involve the formation of several potentially general building blocks.
Efficient synthesis of bongkrekic acid. Three-component convergent strategy
Sato, Yukiko,Aso, Yoshifumi,Shindo, Mitsuru
scheme or table, p. 4164 - 4166 (2009/12/01)
An efficient total synthesis of the apoptosis inhibitor bongkrekic acid was accomplished using a three-component convergent strategy involving a Kocienski-Julia olefination and a Suzuki-Miyaura coupling, in which the longest linear sequence was 18 steps and proceeded in 6.4% overall yield. The torquoselective olefination also contributed to the shortening of the synthesis.
Total synthesis of bongkrekic acid via sequential suzuki-miyaura coupling reactions
Kanematsu, Makoto,Shindo, Mitsuru,Yoshida, Masahiro,Shishido, Kozo
experimental part, p. 2893 - 2904 (2010/03/03)
An efficient total synthesis of (+)-bongkrekic acid, a potent apoptosis inhibitor, has been accomplished by employing a convergent strategy based on the Suzuki-Miyaura coupling of three fully functionalized segments. Georg Thieme Verlag Stuttgart.
Total synthesis of (+)-bongkrekic acid
Shindo, Mitsuru,Sugioka, Tomoyuki,Umaba, Yuko,Shishido, Kozo
, p. 8863 - 8866 (2007/10/03)
Total synthesis of bongkrekic acid, an important apoptosis inhibitor, has been accomplished. The strategy includes inexpensive starting materials, asymmetric alkylation, anionic allyl coupling and oxidative manipulations. This process would provide a sufficient amount of bongkrekic acid and its analogues.
