158980-65-5Relevant academic research and scientific papers
Divergent response of homologous ATP sites to stereospecific ligand fluorination for selectivity enhancement
Patel, Alpesh Ramanlal,Hardianto, Ari,Ranganathan, Shoba,Liu, Fei
supporting information, p. 1570 - 1574 (2017/02/23)
Acquiring a divergent response from homologous protein domains is essential for selective ligand-protein interactions. Stereospecific fluorination of (?)-balanol, an ATP mimic, uncovers a new source of selectivity from integrated chemical and conformational perturbation that differentiates homologous sites by the level of congruency in their response to local and remote fluorine effects.
An efficient approach for the synthesis of the hexahydroazepine segment of balanol
Yadav,Srinivas
, p. 3837 - 3839 (2007/10/03)
An efficient approach for the synthesis of the hexahydroazepine segment of balanol is described in seven steps in a highly stereoselective manner starting from (S)-2,3-O-isopropylidine glyceraldehyde.
An efficient formal synthesis of (-)-balanol by using ruthenium-catalyzed asymmetric hydrogenation
Phansavath, Phannarath,De Paule, Sebastien Duprat,Ratovelomanana-Vidal, Virginie,Genet, Jean-Pierre
, p. 3903 - 3907 (2007/10/03)
An efficient formal synthesis of (-)-balanol is reported. The ten-step sequence leading to a key precursor 4 features a highly stereoselective synthesis of the functionalized hexahydroazepine core through dynamic kinetic resolution of a racemic α-amido β-
Formal Total Synthesis of (-)-Balanol: Concise Approach to the Hexahydroazepine Segment Based on RCM
Fuerstner, Alois,Thiel, Oliver R.
, p. 1738 - 1742 (2007/10/03)
A concise synthesis of the hexahydroazepine moiety 13 of (-)-balanol 1 is described that comprises only eight steps and is distinctly shorter than all previous reported approaches to this particular compound. Sharpless epoxidation of divinylcarbinol 4 and ring closing alkene metathesis (RCM) reaction for the formation of the heterocyclic scaffold 9 constitute the key transformations of this sequence. The latter reaction is best achieved with catalytic amounts of the ruthenium indenylidene complex 18 recently reported. Furthermore, it is demonstrated that RCM can be successfully carried out even in the presence of an azido function provided that Schrock's molybdenum alkylidene complex Mo(=NAr)(=CHCMe2Ph)[OC(Me)(CF3)2]2 (Ar = 2,6-diisopropylphenyl) is used as precatalyst.
Total synthesis of (-)-balanol
Miyabe, Hideto,Torieda, Mayumi,Inoue, Kyoko,Tajiri, Kazumi,Kiguchi, Toshiko,Naito, Takeaki
, p. 4397 - 4407 (2007/10/03)
The efficient total synthesis of (-)-balanol, a potent inhibitor of the protein kinase C, is described (-)-Balanol consists of a chiral hexahydroazepine-containing fragment and a benzophenone fragment, both of which were prepared via novel synthetic routes. The hxahydroazepine fragment was prepared in racemic form through either Bu3SnH- or SmI2-promoted radical cyclization of oxime ethers 2ab intramolecularly connected with the formyl group. SmI2-promoted radical cyclization of 2b was found to be particularly successful in the selective synthesis of the seven-membered trans-amino alcohol 8b. Preparation of the enantiomerically pure hexahydroazepine-containing fragment was achieved through the enantioselective enzymatic acetylation of racemic alcohol 9, employing the immobilized lipase from Pseudomonas sp. The benzophenone fragment was prepared in short steps through a biomimetic oxidative anthraquinone ring cleavage starting from commercially available natural chrysophanic acid 15c. This reaction proceeded via [4 + 2]-cycloaddition of single of oxygen to anthracene derivative 17c, followed by Baeyer-Villiger-type rearrangement of the resulting hydroperoxide to afford the benzophenone derivatives 22 and 23.
Total synthesis of (-)-balanol
Miyabe, Hideto,Torieda, Mayumi,Kiguchi, Toshiko,Naito, Takeaki
, p. 580 - 582 (2007/10/03)
The total synthesis of (-)-balanol, a potent protein kinase C inhibitor, is described. The synthesis includes a radical cyclization approach to the hexahydroazepine-containing fragment and a biomimetic route to the benzophenone fragment.
A novel and chiral synthesis of both enantiomers of trans-3-amino-4- hydroxyhexahydroazepine, a key intermediate for the synthesis of balanol
Naito,Torieda,Tajiri,Ninomiya,Kiguchi
, p. 624 - 626 (2007/10/03)
Both enantiomers of the hexahydroazepine (7), key intermediates for the synthesis of (-)-balanol (1) and its enantiomer, were effectively synthesized via the shortest route involving stannyl radical cyclization of the aldehyde (4) connected with oxime eth
Total synthesis of (-)· and (+)-balanol
Lampe, John W.,Hughes, Philip F.,Biggers, Christopher K.,Smith, Shelley H.,Hu, Hong
, p. 4572 - 4581 (2007/10/03)
Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-∈-caprolactam.
Total Synthesis of (-)-Balanol
Lampe, John W.,Hughes, Philip F.,Biggers, Christopher K.,Smith, Shelley H.,Hu, Hong
, p. 5147 - 5148 (2007/10/02)
(-)-Balanol, a fungal metabolite with potent protein kinase C inhibitory properties, has been prepared in a total synthesis which makes use of an anionic homo-Fries rearrangement approach to the benzophenone subunit and in which the azepane subunit is obt
