158664-40-5Relevant articles and documents
Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I
Makabe, Hidefumi,Kimura, Yuka,Higuchi, Masaharu,Konno, Hiroyuki,Murai, Masatoshi,Miyoshi, Hideto
, p. 3119 - 3130 (2006)
A convergent stereoselective synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin and squamostolide was accomplished via a Pd-catalyzed cross-coupling reaction. The inhibitory activity of these compounds was examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed a remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin. Our results indicate that to maintain potent inhibitory effect, the hydroxylated lactone cannot substitute for the hydroxylated mono- or bis-THF rings with a long alkyl chain that can be seen in ordinary acetogenins.
Total Synthesis of Solamin and Reticulatin
Makabe, Hidefumi,Tanaka, Akira,Oritani, Takayuki
, p. 1975 - 1982 (2007/10/02)
A total synthesis of the natural products, solamin 1 and reticulatin 2 is described.The monotetrahydrofuran moiety 12a of compounds 1 and 2 was constructed by an eight-step reaction sequence, starting from (-)-muricatacin 5, an acetogenin derivative.The γ
