Collect. Czech. Chem. Commun. 2002, 67, 75-82

Synthesis of N-Acetyl-3-phenylisoserinates of Sesquiterpenoid Alcohols of Lactarius Origin

Rafał Baryckia, Maria Gumułkaa, Marek Masnyka, Włodzimierz M. Daniewskia,*, Mirosław Kobusb and Mirosław Łuczakb

a Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland
b Department of Medical Microbiology, Medical University of Warsaw, Poland


Important biological properties of Taxol i.e. 13-N-benzoyl-(2R,3S)-3-phenylisoserinate of baccatin III and also N-benzoyl-(2R,3S)-3-phenylisoserinates of several sesquiterpenoid alcohols of Lactarius origin prompted us to synthesize N-acetyl-3-phenylisoserinates of latter alcohols in order to check and compare their biological properties. Suitably protected phenylisoserine 5 when reacted with sesquiterpenoid alcohols in the presence of DCC gave appropriate esters 7. These, after catalytic hydrogenation deprotection produced aminols 8, which were acetylated and gave the required N-acetyl-3-phenylisoserinates 9a-9g.

Keywords: N-Acetyl-3-phenylisoserine; Sesquiterpenoids; Alcohols; Amino acids; Taxol; Furandiol; Lactarorufin; Lactarius origin.

References: 6 live references.