102989-24-2Relevant articles and documents
Convergent Total Synthesis of Asimicin via Decarbonylative Radical Dimerization
Kawamata, Takahiro,Yamaguchi, Akinori,Nagatomo, Masanori,Inoue, Masayuki
, p. 18907 - 18912 (2018)
Asimicin (1) exhibits potent antitumor activity and comprises a central C2-symmetric bis-tetrahydrofuran and two aliphatic side-chains, one of which terminates with (S)-methyl-2(5H)-furanone. This work reports a convergent total synthesis of 1 in 17 steps from d-gulose derivative 4. Decarbonylative radical-radial homo-coupling of α-alkoxyacyl telluride 12 a efficiently produced the C2-symmetric core 3-SS, which was transformed into 1 through stepwise attachment of the two side-chains and functional group manipulations.
Alteration of the bis-tetrahydrofuran core stereochemistries in asimicin can affect the cytotoxicity
Sinha, Subhash C.,Chen, Zhiyong,Huang, Zheng-Zheng,Nakamaru-Ogiso, Eiko,Pietraszkiewicz, Halina,Edelstein, Matthew,Valeriote, Frederick
supporting information; experimental part, p. 7045 - 7048 (2009/11/30)
A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.
A modular synthesis of annonaceous acetogenins
Marshall, James A.,Piettre, Arnaud,Paige, Mikell A.,Valeriote, Frederick
, p. 1771 - 1779 (2007/10/03)
A synthesis of four Annonaceous acetogenins, asiminocin, asimicin, asimin, and bullanin, by a modular approach from seven fundamental subunits, A-G, is described. The approach employs a central core aldehyde segment, C, to which are appended an aliphatic terminus, A or B, a spacer subunit, D or E, and a butenolide terminus, F or G. Coupling of the A, B, D, and E segments to the core aldehyde unit is effected by highly diastereoselective additions of enantiopure allylic indium or tin reagents. The butenolide termini are attached to the ACD, BCE, or BCD intermediates by means of a Sonogashira coupling. The design of the core, spacer, and termini subunits is such that any of the C30, C10, or C4 natural acetogenins or stereoisomers thereof could be prepared. IC50 values for the four aforementioned acetogenins against H-116 human colon cancer cells were found to be in the 10-3 to 10-4 μM range. The IC90 activities were ca. 10-3 μM for asimicin and asimin but only 0.1-1 μM for bullanin and asiminocin.
