Regioselective domino metathesis of 7-oxanorbornenes and its application to the synthesis of biologically active glutamate analogues

Minoru Ikoma; Masato Oikawa; Martin B. Gill; Geoffrey T. Swanson; Ryuichi Sakai; Keiko Shimamoto; Makoto Sasaki

doi:10.1002/ejoc.200800704

Regioselective domino metathesis of 7-oxanorbornenes and its application to the synthesis of biologically active glutamate analogues

Minoru Ikoma, Masato Oikawa, Martin B. Gill, Geoffrey T. Swanson, Ryuichi Sakai, Keiko Shimamoto, Makoto Sasaki

LIF - Molecular and Chemical Life Science

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5215-5220
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	31
DOIs	https://doi.org/10.1002/ejoc.200800704
Publication status	Published - 2008 Nov

Keywords

Combinatorial chemistry
Domino reactions
Metathesis
Nitrogen heterocycles
Oxygen heterocycles
Regioselectivity

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.200800704

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title = "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.",

keywords = "Combinatorial chemistry, Domino reactions, Metathesis, Nitrogen heterocycles, Oxygen heterocycles, Regioselectivity",

author = "Minoru Ikoma and Masato Oikawa and Gill, {Martin B.} and Swanson, {Geoffrey T.} and Ryuichi Sakai and Keiko Shimamoto and Makoto Sasaki",

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AU - Ikoma, Minoru

AU - Oikawa, Masato

AU - Gill, Martin B.

AU - Swanson, Geoffrey T.

AU - Sakai, Ryuichi

AU - Shimamoto, Keiko

AU - Sasaki, Makoto

PY - 2008/11

Y1 - 2008/11

N2 - 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.

AB - 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.

KW - Combinatorial chemistry

KW - Domino reactions

KW - Metathesis

KW - Nitrogen heterocycles

KW - Oxygen heterocycles

KW - Regioselectivity

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JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

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ER -

Regioselective domino metathesis of 7-oxanorbornenes and its application to the synthesis of biologically active glutamate analogues

Abstract

Keywords

ASJC Scopus subject areas

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