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Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues.

ABSTRACT: A highly regioselective domino metathesis reaction of 7-oxanorbornene was developed that employed an intramolecular association of an amide carbonyl group to a ruthenium metal centre. By using this reaction, twelve glutamate analogues inspired by dysiherbaine were efficiently synthesized over 12-14 steps; one of the analogues exhibited bioactivity consistent with central nervous system depression.

SUBMITTER: Ikoma M 

PROVIDER: S-EPMC2717718 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues.

Ikoma Minoru M   Oikawa Masato M   Gill Martin B MB   Swanson Geoffrey T GT   Sakai Ryuichi R   Shimamoto Keiko K   Sasaki Makoto M  

European journal of organic chemistry 20081101 31

A highly regioselective domino metathesis reaction of 7-oxanorbornene was developed that employed an intramolecular association of an amide carbonyl group to a ruthenium metal centre. By using this reaction, twelve glutamate analogues inspired by dysiherbaine were efficiently synthesized over 12-14 steps; one of the analogues exhibited bioactivity consistent with central nervous system depression. ...[more]

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