Asymmetric total synthesis and stereochemical elucidation of the antitumor agent PM-94128.
[reaction: see text]. PM-94128, a novel depsipeptide antitumor agent, has been synthesized for the first time through a highly stereocontrolled route. The key steps for the synthesis of the dihydroxyamino acid moiety involve a diastereoselective addition of tert-butyl lithiopropiolate to a chiral nitrone and a 2,3-dihydro[1,2]oxazin-6-one dihydroxylation. The synthesis serves to define the relative as well as the absolute configuration of the natural product (bearing five stereogenic centers).
LEDSS, UMR 5616 CNRS, Institut de Chimie Moléculaire de Grenoble - FR2607, Université Joseph Fourier, B.P. 53, 38041 Grenoble, France.
Samir K
SK
Patel
Karine
K
Murat
Sandrine
S
Py
Yannick
Y
Vallée