Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein

Mette T. Petersen; Thomas Eiland Nielsen

doi:10.1021/ol400654r

Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein

Mette T. Petersen, Thomas Eiland Nielsen

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

Original language	English
Journal	Organic Letters
Volume	15
Issue number	8
Pages (from-to)	1986-1989
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol400654r
Publication status	Published - 2013

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10.1021/ol400654r

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title = "Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein",

abstract = "A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.",

author = "Petersen, {Mette T.} and Nielsen, {Thomas Eiland}",

year = "2013",

doi = "10.1021/ol400654r",

language = "English",

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T1 - Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein

AU - Petersen, Mette T.

AU - Nielsen, Thomas Eiland

PY - 2013

Y1 - 2013

N2 - A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

AB - A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

U2 - 10.1021/ol400654r

DO - 10.1021/ol400654r

M3 - Journal article

C2 - 23550830

VL - 15

SP - 1986

EP - 1989

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 8

ER -