Marie-Thérèse Le Goff

Rearrangement reactions of taxanes: structural modifications of 10-deacetylbaccatin III.

Abstract 10-Deacetylbaccatin III 2 is a taxane diterpenoid isolated from the plant genus Taxus , which has been used for the partial sythesis of the antitumor compounds taxol and taxotere®. A number of structural modifications have been performed on 2 under acidic and basic conditions in order to obtain new synthetic precursors of taxol and taxotere® analogues.

An unequivocal synthesis of 1-benzyl-3-ethyl-1,6-dihydropyridine and its use for a biogenetically modelled synthesis of (±)-catharanthine

The first unambiguous synthesis of an N-substituted 3-ethyl-1,6-dihydropyridine (2) and its use for a biomimetic synthesis of (±)-catharanthine (4) are described.

Use of tetrabutylammonium cyanide for photocyanation of aromatic compounds: phase transfer photochemistry

Nucleophilic aromatic photosubstitution can be carried out using tetrabutylammonium cyanide in anhydrous acetonitrile or methylene chloride and also under phase-transfer conditions (CH2Cl2–KCN in H2O).

Use of crown ethers for photochemical cyanation of aromatic hydrocarbons

The photocyanation of the aromatic hydrocarbons naphthalene, anthracene, phenanthrene, and biphenyl occurs easily with potassium cyanide dissolved by means of the cyclic polyether 18-crown-6 in anhydrous acetonitrile.

PHOTOCHEMISCHE RK. 20.MITT. PHOTO‐FRIES‐RK. IN DER HETEROCYCLISCHEN REIHE 5.MITT. EINFLUSS DER ELEKTRONEN GEBENDEN UND ELEKTRONEN ZIEHENDEN SUBSTITUENTEN AUF DIE PHOTOCHEMISCHE REAKTIVITAET DER ESTER VON HYDROXYPYRIDINEN UND NICOTINSAEUREPHENYLESTERN

Eine Abhangigkeit der photochemischen Reaktivitat von den funktionellen Gruppen der Acyl-Gruppe, wie sie bei Benzoesaurephenylestern festgestellt wurde, besteht bei den Estern (I) bzw. (II) nicht.

PHOTOCHEMISCHE CYCLOADDITIONEN, DARST. VON CYCLOBUTANDERIVATEN DER PYRIMIDIN- UND KOHLENHYDRAT-REIHE

Bei Bestrahlung einer Acetonlosung des Pyrimidins (I) in Gegenwart des cyclischen Carbonats (II) tritt Cycloaddition unter Bildung der isomeren Verbindungen (III) und (IV) (1:1-Verhaltnis) ein.