158705-53-4Relevant academic research and scientific papers
Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I
Makabe, Hidefumi,Hattori, Yasunao,Kimura, Yuka,Konno, Hiroyuki,Abe, Masato,Miyoshi, Hideto,Tanaka, Akira,Oritani, Takayuki
, p. 10651 - 10657 (2004)
A convergent total synthesis of cis-solamin (1a) and its diastereomer (1b) was accomplished. A key reaction of this approach was the use of VO(acac) 2-catalyzed diastereoselective epoxidation of (Z)-bis-homoallylic alcohol 3 followed by spontaneous cyclization for the cis-THF ring formation. By comparison of the optical rotation of the two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a. Inhibitory action of synthetic 1a and 1b with bovine heart mitochondrial complex I are reported. Graphical Abstract.
Total synthesis of cis-solamin.
Makabe, Hidefumi,Hattori, Yasunao,Tanaka, Akira,Oritani, Takayuki
, p. 1083 - 1085 (2007/10/03)
[structure: see text] A convergent total synthesis of cis-solamin and its diastereomer was accomplished using VO(acac)2-catalyzed diastereoselective epoxidation followed by cyclization of bis-homoallylic alcohol as the key step. By comparison of the optic
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
