Stereoselective synthesis of cis-2,5-disubstituted THFs: application to adjacent bis-THF cores of Annonaceous acetogenins.
The iodocyclization of γ,δ-unsaturated alcohols in the presence of a silyl enol ether produced cis-2,5-disubstituted tetrahydrofurans in one pot via siloxy intermediates. N-Iodosuccinimide (NIS) effectively worked as an activator of the double bonds in the substrates and the silyl enol ether. Application to an expedient synthesis of the adjacent bis-tetrahydrofuran core of Annonaceous acetogenins with a cis/threo/cis relative stereochemistry is also described.
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871 Japan. fujioka@phs.osaka-u.ac.jp
Hiromichi
H
Fujioka
Ryota
R
Maehata
Shintaro
S
Wakamatsu
Kenji
K
Nakahara
Tatsuya
T
Hayashi
Tomohiro
T
Oki
D029061:Annonaceae / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis; D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D001688:Biological Products; D005663:Furans; C018674:tetrahydrofuran