Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

Cong Ma; Aurélien Letort; Rémi Aouzal; Antonia Wilkes; Gourhari Maiti; Louis J. Farrugia; Louis Ricard; Joëlle Prunet

doi:10.1002/chem.201600592

Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

Cong Ma, Aurélien Letort, Rémi Aouzal, Antonia Wilkes, Gourhari Maiti, Louis J. Farrugia, Louis Ricard, Joëlle Prunet

Research output: Journal article publication › Journal article › Academic research › peer-review

18 Citations (Scopus)

Abstract

KGaA, Weinheim. Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring-closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem-dimethyl group), the RCEDYM reaction leads to 14,15-isotaxanes 16 a,b and 18 b with the gem-dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem-dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring-closing metathesis reaction, to give the tricyclic core of Taxol 44.

Original language	English
Pages (from-to)	6891-6898
Number of pages	8
Journal	Chemistry - A European Journal
Volume	22
Issue number	20
DOIs	https://doi.org/10.1002/chem.201600592
Publication status	Published - 10 May 2016
Externally published	Yes

Keywords

cyclooctenes
enyne
metathesis
synthesis design
taxanes

ASJC Scopus subject areas

General Chemistry

More information

10.1002/chem.201600592

Cite this

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title = "Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives",

abstract = "KGaA, Weinheim. Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring-closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem-dimethyl group), the RCEDYM reaction leads to 14,15-isotaxanes 16 a,b and 18 b with the gem-dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem-dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring-closing metathesis reaction, to give the tricyclic core of Taxol 44.",

keywords = "cyclooctenes, enyne, metathesis, synthesis design, taxanes",

author = "Cong Ma and Aur{\'e}lien Letort and R{\'e}mi Aouzal and Antonia Wilkes and Gourhari Maiti and Farrugia, {Louis J.} and Louis Ricard and Jo{\"e}lle Prunet",

year = "2016",

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day = "10",

doi = "10.1002/chem.201600592",

language = "English",

volume = "22",

pages = "6891--6898",

journal = "Chemistry - A European Journal",

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T1 - Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

AU - Ma, Cong

AU - Letort, Aurélien

AU - Aouzal, Rémi

AU - Wilkes, Antonia

AU - Maiti, Gourhari

AU - Farrugia, Louis J.

AU - Ricard, Louis

AU - Prunet, Joëlle

PY - 2016/5/10

Y1 - 2016/5/10

N2 - KGaA, Weinheim. Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring-closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem-dimethyl group), the RCEDYM reaction leads to 14,15-isotaxanes 16 a,b and 18 b with the gem-dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem-dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring-closing metathesis reaction, to give the tricyclic core of Taxol 44.

AB - KGaA, Weinheim. Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring-closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem-dimethyl group), the RCEDYM reaction leads to 14,15-isotaxanes 16 a,b and 18 b with the gem-dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem-dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring-closing metathesis reaction, to give the tricyclic core of Taxol 44.

KW - cyclooctenes

KW - enyne

KW - metathesis

KW - synthesis design

KW - taxanes

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U2 - 10.1002/chem.201600592

DO - 10.1002/chem.201600592

M3 - Journal article

C2 - 27062670

SN - 0947-6539

VL - 22

SP - 6891

EP - 6898

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 20

ER -

Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

Abstract

Keywords

ASJC Scopus subject areas

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