Total synthesis of sphingofungin E from D-glucose.
[reaction: see text] Total synthesis of sphingofungin E (1) is described. Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose generated tetra-substituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized part in sphingofungin E (4) stereoselectively. Coupling reaction of 4 with the C(12) hydrophobic part, followed by further manipulation, completed the total synthesis.
Oishi
Takeshi
T
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522 Japan.
Ando
Koji
K
Inomiya
Kenjin
K
Sato
Hideyuki
H
Iida
Masatoshi
M
Chida
Noritaka
N
D000596:Amino Acids / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry*; D007202:Indicators and Reagents; D013237:Stereoisomerism
D000596:Amino Acids; D000935:Antifungal Agents; D005231:Fatty Acids, Unsaturated; D007202:Indicators and Reagents; C078943:sphingofungin E; D005947:Glucose