163082-04-0Relevant articles and documents
Several generations of chemoenzymatic synthesis of oseltamivir (Tamiflu): Evolution of strategy, quest for a process-quality synthesis, and evaluation of efficiency metrics
Werner, Lukas,Machara, Ales,Sullivan, Bradford,Carrera, Ignacio,Moser, Michael,Adams, David R.,Hudlicky, Tomas,Andraos, John
, p. 10050 - 10067 (2012/01/15)
Four generations of chemoenzymatic approaches to oseltamivir are presented. The first two generations relied on the use of cyclohexadiene-cis-diol derived enzymatically from bromobenzene. The third and fourth generation used the corresponding diol obtaine
Cyclotrimerization approach to unnatural structural modifications of pancratistatin and other amaryllidaceae constituents - Synthesis and biological evaluation
Hudlicky, Tomas,Moser, Michael,Banfield, Scott C.,Rinner, Uwe,Chapuis, Jean-Charles,Pettit, George R.
, p. 1313 - 1337 (2007/10/03)
The phenanthridone core of pancratistatin lacking all aromatic oxygenation was prepared by cyclotrimerization of acetylene-containing scaffolds 30 and 41, reflecting the natural and the C-1 epi configuration, respectively, of the amino inositol moiety. Th
Total synthesis and biological evaluation of Amaryllidaceae alkaloids: narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives.
Hudlicky, Tomas,Rinner, Uwe,Gonzalez, David,Akgun, Hulya,Schilling, Stefan,Siengalewicz, Peter,Martinot, Theodore A,Pettit, George R
, p. 8726 - 8743 (2007/10/03)
Biocatalytic approaches have yielded efficient total syntheses of the major Amaryllidaceae alkaloids, all based on the key enzymatic dioxygenation of suitable aromatic precursors. This paper discusses the logic of general synthetic design for lycoricidine, narciclasine, pancratistatin, and 7-deoxypancratistatin. Experimental details are provided for the recently accomplished syntheses of narciclasine, ent-7-deoxypancratistatin, and 10b-epi-deoxypancratistatin via a new and selective opening of a cyclic sulfate over aziridines followed by aza-Payne rearrangement. The structural core of 7-deoxypancratistatin has also been degraded to a series of intermediates in which the amino inositol unit is cleaved and deoxygenated in a homologous fashion. These truncated derivatives and the compounds from the synthesis of the unnatural derivatives have been tested against six important human cancer cell lines in an effort to further develop the understanding of the mode of action for the most active congener in this group, pancratistatin. The results of the biological activity testing as well as experimental, spectral, and analytical data are provided in this manuscript for all relevant compounds.
Synthesis, structure, and biological evaluation of novel N- and O-linked diinositols
Paul, Bernhard J.,Willis, Jerremey,Martinot, Theodore A.,Ghiviriga, Ion,Abboud, Khalil A.,Hudlicky, Tomas
, p. 10416 - 10426 (2007/10/03)
Several O-and N-linked inositols and/or aminoinositols have been prepared by iterative opening of epoxides and aziridines derived from homochiral cyclohexadiene cis-diols. The three inositols and their intermediate conduritols (conduramines) were tested a
Structure assignment of aminoconduritols by 15N NMR correlation spectroscopy; synthesis of a positional isomer of 7-deoxypancratistatin
Schilling, Stefan,Rinner, Uwe,Chan, Collin,Ghiviriga, Ion,Hudlicky, Tomas
, p. 1659 - 1667 (2007/10/03)
A positional isomer of 7-deoxypancratistatin was synthesized in 12 steps from epoxyaziridines 4 and 5. An intermolecular opening of the aziridine rather than the epoxide in the early stages of the synthesis led to 13, which did not match the properties of
Toluene dioxygenase-mediated cis-dihydroxylation of aromatics in enantioselective synthesis. Asymmetric total syntheses of pancratistatin and 7-deoxypancratistatin, promising antitumor agents
Hudlicky, Tomas,Tian, Xinrong,K?nigsberger, Kurt,Maurya, Rakesh,Rouden, Jacques,Fan, Boreas
, p. 10752 - 10765 (2007/10/03)
Whole-cell biooxidation of bromobenzene with Pseudomonas putida 39D or the recombinant Escherichia coli JM109 (pDTG601) yields (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (9a), which is protected as the acetonide and converted to vinylaziridines 7, 15a, 6