84236-97-5Relevant academic research and scientific papers
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 (1999)
(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.
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.).
Cyclopropanation by Gold- or Zinc-Catalyzed Retro-Buchner Reaction at Room Temperature
Mato, Mauro,Herlé, Bart,Echavarren, Antonio M.
supporting information, p. 4341 - 4345 (2018/07/29)
Through the design of a second generation of more reactive 7-substituted 1,3,5-cycloheptatrienes, a room-temperature gold(I)-catalyzed retro-Buchner-cyclopropanation sequence and the first zinc(II)-catalyzed version of this process, which uses inexpensive
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 (11R,12S)-lactobacillic acid and its enantiomer
Coxon, Geoffrey D.,Al-Dulayymi, Juma R.,Baird, Mark S.,Knobl, Stefan,Roberts, Evan,Minnikin, David E.
, p. 1211 - 1222 (2007/10/03)
(11R,12S)-Lactobacillic acid has been prepared from 2,3-O-isopropylidene-D-glyceraldehyde, in a sequence involving asymmetric cyclopropanation, and from cis-cyclopropane-1,2-dimethanol, using enzymatic desymmetrisation. The key step in the former route wa
An Unexpected Reversal of Fluorine Substituent Effects in the Biomethylenation of Two Positional Isomers: A Serendipitous Discovery
Buist, Peter H.,Pon, Robert A.
, p. 6240 - 6241 (2007/10/02)
The mechanism of biological cyclopropyl fatty acid biosynthesis as it occurs in Lactobacillus plantarum has been probed using fluorine substituent effects.It has been shown that the pattern of rate retardations induced by homoallylic fluorine substitution is numerically the same but opposite in sense for two series of olefinic fatty acid substrates bearing the double bond at either the 9- or the 11-position.
