692288-05-4Relevant articles and documents
Total Synthesis of Cardiolipins Containing Chiral Cyclopropane Fatty Acids
Inuki, Shinsuke,Ohta, Ippei,Ishibashi, Shunichi,Takamatsu, Masayuki,Fukase, Koichi,Fujimoto, Yukari
, p. 7832 - 7838 (2017/08/14)
Cardiolipin (CL) is a phospholipid located in both the eukaryotic mitochondrial inner membrane and the bacterial cell membrane. Some bacterial CLs are known to contain cyclopropane moieties in their acyl chains. Although the CLs are thought to be involved in the innate immune response, there have been few attempts at chemical synthesis of the CLs, and detailed studies of their biological activities are scarce. Thus, we have developed a synthetic route to CLs containing chiral cyclopropane moieties.
Process development on an efficient new convergent formal synthesis of MIV-150
Cai, Shaopei,Dimitroff, Martin,McKennon, Tracey,Reider, Malcolm,Robarge, Lonnie,Ryckman, David,Shang, Xiao,Therrien, Joseph
, p. 353 - 359 (2013/09/05)
Starting from a known linear route and a proposed convergent route, we have successfully developed a new hybrid convergent route to MIV-150 that takes advantage of the robust chemistry for the preparation of a fluoroketal and the stereospecific Negishi coupling of an iodocyclopropane moiety to a benzene ring. Stereoselective β- and cis-iodination chemistry was developed for the preparation of an enantiomerically pure iodocyclopropanecarboxylate. Following the Negishi coupling, proven chemistry from the linear route was incorporated, thus ensuring a similar high-purity profile for the final active pharmaceutical ingredient (API). In addition, we have prepared and evaluated a series of basic inorganic and organic MIV-150 salts that have drastically increased water solubility over the parent compound.
