Diastereoselective two-directional synthesis and cation transport ability of the central tristetrahydrofuranyl unit of meso polyether glabrescol as naturally occurring podand.
The diastereoselective synthesis of the central 2,5-linked tristetrahydrofuran (trisTHF) 6 of naturally occurring meso polyether, glabrescol (5), has been achieved in a two-directional manner by the vanadium(V)-catalyzed anti oxidative cyclizations of diol 14. The trisTHF podand 6 and its stereoisomeric analogs 7 and 8 exhibited outstanding cation transport abilities for physiologically important Na+ and K+.
Morimoto
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Y
Department of Chemistry, Graduate School of Science, Osaka City University, Japan. morimoto@sci.osaka-cu.ac.jp
Iwai
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T
Yoshimura
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T
Kinoshita
T
T
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002412:Cations; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017136:Ion Transport; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000972:Antineoplastic Agents, Phytogenic; D002412:Cations; D005663:Furans; C116803:glabrescol