83447-87-4Relevant articles and documents
Synthesis of Cyclopropane Fatty Acids by C(sp3)?C(sp3) Cross-Coupling Reaction and Formal Synthesis of α-Mycolic Acid
Iwasaki, Takanori,Terahigashi, Shohei,Wang, Yufei,Tanaka, Arisa,Zhao, Hanqing,Fujimoto, Yukari,Fukase, Koichi,Kambe, Nobuaki
, p. 3810 - 3817 (2018/09/18)
An iterative Ni-catalyzed C(sp3)?C(sp3) cross-coupling reaction of a novel cis-cyclopropane containing bifunctional building blocks with alkyl halides and alkyl Grignard reagents enabled the introduction of a cyclopropane ring into the desired position(s) of saturated carbon frameworks, providing a straightforward synthetic route to cyclopropane fatty acids. The present method creates a direct route for the construction of saturated carbon frameworks, and can avoid the tedious multistep operations based on unsaturated functional group manipulations that are often employed in conventional synthetic routes. This method could be applicable to the synthesis of trans-cyclopropane fatty acids and enantioenriched cyclopropane fatty acids. Formal synthesis of α-mycolic acid was achieved by the C(sp3)?C(sp3) cross-coupling reaction of cyclopropane-containing bifunctional building blocks. (Figure presented.).
Total syntheses of cis-cyclopropane fatty acids: Dihydromalvalic acid, dihydrosterculic acid, lactobacillic acid, and 9,10-methylenehexadecanoic acid
Shah, Sayali,White, Jonathan M.,Williams, Spencer J.
, p. 9427 - 9438 (2014/12/11)
cis-Cyclopropane fatty acids (cis-CFAs) are widespread constituents of the seed oils of subtropical plants, membrane components of bacteria and protozoa, and the fats and phospholipids of animals. We describe a systematic approach to the synthesis of enan
The synthesis of both enantiomers of lactobacillic acid and mycolic acid analogues
Coxon, Geoffrey D.,Knobl, Stefan,Roberts, Evan,Baird, Mark S.,Al Dulayymi, Juma R.,Besra, Gurdyal S.,Brennan, Patrick J.,Minnikin, David E.
, p. 6689 - 6692 (2007/10/03)
(11R, 12S)-Lactobacillic acid (1) has been prepared either from D- mannitol by asymmetric cyclopropanation or from cis-cyclopropane-1, 2- dimethanol by enzymatic desymmetrisation. The syntheses of (l1S 12R)- lactobacillic acid (2) and (1R, 2S) 1- (3'-methoxycarbonylpropyl)-2- octadecylcyclopropane (26) and related analogues (27 and 28) have also been achieved.