Total synthesis of cis-solamin.
[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 optical rotation of two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a.
Makabe
Hidefumi
H
Graduate School of Agriculture, Sciences of Functional Foods, Integrated Department, Shinshu University, 8304 Mimamiminowa Kamiina, Nagano 399-4598, Japan. makabeh@gipmc.shinshu-u.ac.jp
Hattori
Yasunao
Y
Tanaka
Akira
A
Oritani
Takayuki
T
D029061:Annonaceae / Q000737:chemistry*; D001558:Benzethonium / Q000138:chemical synthesis*; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D013237:Stereoisomerism
D004852:Epoxy Compounds; D007202:Indicators and Reagents; D001558:Benzethonium