Total synthesis of merrilactone A.
Merrilactone A (1) has been shown to possess neurotrophic activity and thus is expected to hold therapeutic potential in the treatment of neurodegeneration diseases. In this paper, we report the total synthesis of (+/-)-1, employing, as key steps, a novel desymmetrization protocol of meso-diketone to construct the core cis-bicyclo[3.3.0]octyl system of 1 (3 --> 2) and a radical cyclization to install the highly congested C9-quaternary carbon (16 --> 17).
Inoue
Masayuki
M
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. inoue@ykbsc.chem.tohoku.ac.jp
Sato
Takaaki
T
Hirama
Masahiro
M
D029523:Illicium / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D012717:Sesquiterpenes / Q000138:chemical synthesis*
D007783:Lactones; D012717:Sesquiterpenes; C458341:merrilactone A