- Towards the synthesis of bisubstrate inhibitors of protein farnesyltransferase: Synthesis and biological evaluation of new farnesylpyrophosphate analogues
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Protein farnesyltransferase (FTase) has recently appeared as a new target of parasitic diseases, a field poor in drugs in development. With the aim of creating new bisubstrate inhibitors of FTase, new farnesyl pyrophosphate analogues have been studied. Fa
- Duez, Stéphanie,Coudray, La?titia,Mouray, Elisabeth,Grellier, Philippe,Dubois, Jo?lle
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experimental part
p. 543 - 556
(2010/05/02)
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- Synthesis of rac-hippospongic acid A and revision of the structure
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rac-Hippospongic acid A of the reported structure 1 and the revised structure 2 were synthesized. The synthetic strategy of these compounds consists of homologation of (2E,6E,10E)-geranylgeraniol and (2E,6E)-farnesol, respectively, Wadsworth-Emmons reaction, and cyclization to form the tetrahydropyran ring bearing an α-methylene group on the carboxylic moiety. Spectral comparisons of the synthetic compounds 1,2 and the natural product suggested that hippospongic acid A bears the structure of 2.
- Tokumasu, Munetaka,Ando, Hiroshi,Hiraga, Yoshikazu,Kojima, Satoshi,Ohkata, Katsuo
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p. 489 - 496
(2007/10/03)
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- Stereoselective syntheses of (+)-rhopaloic acid A and (-)-ent- and (±)-rac-rhopaloic acid A
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Rhopaloic acid A (+)-1 and the related compounds (-)-ent-1 and (±)-rac-1 have been stereoselectively synthesized. The synthetic strategy consists of successive homologation of (2E,6E)-farnesol 7 and cyclization to form a tetrahydropyran ring, together wit
- Takagi, Ryukichi,Sasaoka, Asami,Nishitani, Hiroko,Kojima, Satoshi,Hiraga, Yoshikazu,Ohkata, Katsuo
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p. 925 - 934
(2007/10/03)
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- Synthesis of norsesterterpene rac- and ent-rhopaloic acid A
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The stereoselective synthesis of rac- and ent-rhopaloic acid A 1 has been accomplished, via successive homologation of (2E,6E)-farnesol 2 and cyclization to form a tetrahydropyran ring, together with final introduction of an α-methylene group; the asymmet
- Takagi, Ryukichi,Sasaoka, Asami,Kojima, Satoshi,Ohkata, Katsuo
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p. 1887 - 1888
(2007/10/03)
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- Stereochemical Studies on Porphyrin a: Assignment of the Absolute Configuration of a Model Porphyrin by Degradation
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The synthesis is described of a porphyrin alcohol (22) which has a structure very similar to that of porphyrin a (2).The model porphyrin was resolved by separation of its camphanate esters.Ozonolysis of the 2-nitrobenzoate of each enantiomer in tritiated form gave a derivative of 2-hydroxypentadioic acid whose configuration was determined by dilution analysis.It is demonstrated that correlation of the stereochemistry of porphyrin a with that of the model (22) will be possible by means of the (1)H and (19)F n.m.r. spectra of the corresponding esters with (-)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid.
- Battersby, Alan R.,Cardwell, Kevin S.,Leeper, Finian J.
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p. 1565 - 1580
(2007/10/02)
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