Synthesis of (--)-Muricatacin via alpha- and alpha'-C-H bond functionalization of tetrahydrofuran.
(--)-Muricatacin, a potent cytotoxic (4R,5R)-5-hydroxyheptadecan-4-olide, has been synthesized through alpha-C--H hydroxyalkylation and alpha'-C--H oxidation of tetrahydrofuran. This study presents a novel method for C--H bond functionalization as a means for preparing gamma-(hydroxyalkyl)-gamma-butyrolactones.
Yoshimitsu
Takehiko
T
Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan. takey@my-pharm.ac.jp
Makino
Toshiyuki
T
Nagaoka
Hiroto
H
D000478:Alkylation; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry
D000970:Antineoplastic Agents; D005663:Furans; C082488:muricatacin; C018674:tetrahydrofuran