186641-76-9Relevant academic research and scientific papers
Highly stereocontrolled total synthesis of β-d-mannosyl phosphomycoketide: A natural product from mycobacterium tuberculosis
Li, Nan-Sheng,Scharf, Louise,Adams, Erin J.,Piccirilli, Joseph A.
, p. 5970 - 5986 (2013/07/26)
β-d-Mannosyl phosphomycoketide (C32-MPM), a naturally occurring glycolipid found in the cell walls of Mycobacterium tuberculosis, acts as a potent antigen to activate T-cells upon presentation by CD1c protein. The lipid portion of C32-MPM contains a C32-mycoketide, consisting of a saturated oligoisoprenoid chain with five chiral methyl branches. Here we develop several stereocontrolled approaches to assemble the oligoisoprenoid chain with high stereopurity (>96%) using Julia-Kocienski olefinations followed by diimide reduction. By careful choice of olefination sites, we could derive all chirality from a single commercial compound, methyl (2S)-3-hydroxy-2-methylpropionate (>99% ee). Our approach is the first highly stereocontrolled method to prepare C32-MPM molecule with >96% stereopurity from a single >99% ee starting material. We anticipate that our methods will facilitate the highly stereocontrolled synthesis of a variety of other natural products containing chiral oligoisoprenoid-like chains, including vitamins, phytol, insect pheromones, and archaeal lipids.
Synthesis of stereopure acyclic 1,5-dimethylalkane chirons: Building blocks of highly methyl-branched natural products
Li, Nan-Sheng,Piccirilli, Joseph A.
, p. 9633 - 9641 (2013/10/22)
An efficient synthetic method towards stereopure acyclic 1,5-dimethylalkane building blocks from methyl (2R)-3-hydroxy-2-methylpropionate (R)-1 (>99% ee) and methyl (2S)-3-hydroxy-2-methylpropionate (S)-1 (>99% ee) through a series of chemical transformat
Anti-AIDS agents 81. design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors
Qian, Keduo,Kuo, Reen-Yun,Chen, Chin-Ho,Huang, Li,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
experimental part, p. 3133 - 3141 (2010/09/18)
In our continuing study of triterpene derivatives as potent anti-HIV agents, different C-3 conformationally restricted betulinic acid (BA, 1) derivatives were designed and synthesized in order to explore the conformational space of the C-3 pharmacophore. 3-O-Monomethylsuccinyl-betulinic acid (MSB) analogues were also designed to better understand the contribution of the C-3′ dimethyl group of bevirimat (2), the first-in-class HIV maturation inhibitor, which is currently in phase IIb clinical trials. In addition, another triterpene skeleton, moronic acid (MA, 3), was also employed to study the influence of the backbone and the C-3 modification toward the anti-HIV activity of this compound class. This study enabled us to better understand the structure-activity relationships (SAR) of triterpene-derived anti-HIV agents and led to the design and synthesis of compound 12 (EC50: 0.0006 μM), which displayed slightly better activity than 2 as a HIV-1 maturation inhibitor.
Anti-AIDS agents 73: Structure-activity relationship study and asymmetric synthesis of 3-O-monomethylsuccinyl-betulinic acid derivatives
Qian, Keduo,Nakagawa-Goto, Kyoko,Yu, Donglei,Morris-Natschke, Susan L.,Nitz, Theodore J.,Kilgore, Nicole,Allaway, Graham P.,Lee, Kuo-Hsiung
, p. 6553 - 6557 (2008/03/18)
3-O-3′(or 2′)-Methylsuccinyl-betulinic acid (MSB) derivatives were separated by using recycle HPLC. The structures of four isomers were assigned by NMR and asymmetric synthesis. 3-O-3′S-Methylsuccinyl-betulinic acid (3′S-MSB, 4) exhibited potent anti-HIV
Absolute configuration of nafuredin, a new specific NADH-fumarate reductase inhibitor
Takano, Daisuke,Nagamitsu, Tohru,Ui, Hideaki,Shiomi, Kazuro,Yamaguchi, Yuuichi,Masuma, Rokuro,Kuwajima, Isao,Mura, Satoshi
, p. 3017 - 3020 (2007/10/03)
Nafuredin, a new specific NADH-fumarate reductase inhibitor, was isolated from the culture broth of a fungal strain Aspergillus niger FT-0554. The stereoselective synthesis of three degradation products obtained by ozonolysis of nafuredin allowed elucidation of the absolute configuration of nafuredin.
Synthetic studies on halichondrin B, an antitumor polyether macrolide isolated from a marine sponge. 9. Synthesis of the C16 - C36 unit via stereoselective construction of the D and E rings
Horita, Kiyoshi,Nagasawa, Masaaki,Sakurai, Youji,Yonemitsu, Osamu
, p. 1199 - 1216 (2007/10/03)
The C16 - C36 unit of halichondrin B was stereoselectively synthesized via the aldol condensation of two C16 - C26 esters with the previously synthesized C27 - C36 aldehyde followed by E ring construction. The C16 - C26 esters were prepared starting from (2S)-3-hydroxy-2-methylpropionic acid and L-tartaric acid via construction of the D ring by iodoetherification.
Synthesis of optically active diastereomers of a nonproteic neurotrophic mimetic
Keyling-Bilger, Florence,Schmitt, Gaby,Beck, Alain,Luu, Bang
, p. 14891 - 14904 (2007/10/03)
The four diastereomers 3, elongated analogues of perhydroretinol, are synthesized starting from both optically pure 3-bromo-2-methyl-1-propanol enantiomers. All exhibit neurotrophic activity on cultured neuronal cells derived from fetal rat cerebral hemispheres.
