Generation of a Heteropolycyclic and sp3-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence

Thomas Flagstad; Carlos M.G. Azevedo; Nikolaj S. Troelsen; Geanna K. Min; Yohan Macé; Anthony Willaume; Rachel Guilleux; Mélanie Velay; Karine Bonnet; Remy Morgentin; Thomas E. Nielsen; Mads H. Clausen

doi:10.1002/ejoc.201801551

Generation of a Heteropolycyclic and sp³-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence

Thomas Flagstad, Carlos M.G. Azevedo, Nikolaj S. Troelsen, Geanna K. Min, Yohan Macé, Anthony Willaume, Rachel Guilleux, Mélanie Velay, Karine Bonnet, Remy Morgentin, Thomas E. Nielsen^*, Mads H. Clausen

^*Corresponding author af dette arbejde

2 Citationer (Scopus)

Abstract

Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is available through a one-pot Petasis 3-component reaction/Diels–Alder cascade reaction. We demonstrate the versatility of the approach through the synthesis of 35 exemplary compounds from the three classes, as well as by the production of 2188 final compounds, which have been included in the Joint European Compound Library of the European Lead Factory.

Originalsprog	Engelsk
Tidsskrift	European Journal of Organic Chemistry
Vol/bind	2019
Udgave nummer	5
Sider (fra-til)	1061-1076
ISSN	1434-193X
DOI	https://doi.org/10.1002/ejoc.201801551
Status	Udgivet - 7 feb. 2019

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10.1002/ejoc.201801551

Citationsformater

Flagstad, T., Azevedo, C. M. G., Troelsen, N. S., Min, G. K., Macé, Y., Willaume, A., Guilleux, R., Velay, M., Bonnet, K., Morgentin, R., Nielsen, T. E., & Clausen, M. H. (2019). Generation of a Heteropolycyclic and sp³-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence. European Journal of Organic Chemistry, 2019(5), 1061-1076. https://doi.org/10.1002/ejoc.201801551

Generation of a Heteropolycyclic and sp³-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence. / Flagstad, Thomas; Azevedo, Carlos M.G.; Troelsen, Nikolaj S. et al.

I: European Journal of Organic Chemistry, Bind 2019, Nr. 5, 07.02.2019, s. 1061-1076.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Flagstad, T, Azevedo, CMG, Troelsen, NS, Min, GK, Macé, Y, Willaume, A, Guilleux, R, Velay, M, Bonnet, K, Morgentin, R, Nielsen, TE & Clausen, MH 2019, 'Generation of a Heteropolycyclic and sp³-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence', European Journal of Organic Chemistry, bind 2019, nr. 5, s. 1061-1076. https://doi.org/10.1002/ejoc.201801551

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title = "Generation of a Heteropolycyclic and sp3-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence",

abstract = "Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is available through a one-pot Petasis 3-component reaction/Diels–Alder cascade reaction. We demonstrate the versatility of the approach through the synthesis of 35 exemplary compounds from the three classes, as well as by the production of 2188 final compounds, which have been included in the Joint European Compound Library of the European Lead Factory.",

keywords = "Cycloaddition, Drug discovery, Heterocycles, Library synthesis",

author = "Thomas Flagstad and Azevedo, {Carlos M.G.} and Troelsen, {Nikolaj S.} and Min, {Geanna K.} and Yohan Mac{\'e} and Anthony Willaume and Rachel Guilleux and M{\'e}lanie Velay and Karine Bonnet and Remy Morgentin and Nielsen, {Thomas E.} and Clausen, {Mads H.}",

year = "2019",

month = feb,

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doi = "10.1002/ejoc.201801551",

language = "English",

volume = "2019",

pages = "1061--1076",

journal = "European Journal of Organic Chemistry",

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AU - Flagstad, Thomas

AU - Azevedo, Carlos M.G.

AU - Troelsen, Nikolaj S.

AU - Min, Geanna K.

AU - Macé, Yohan

AU - Willaume, Anthony

AU - Guilleux, Rachel

AU - Velay, Mélanie

AU - Bonnet, Karine

AU - Morgentin, Remy

AU - Nielsen, Thomas E.

AU - Clausen, Mads H.

PY - 2019/2/7

Y1 - 2019/2/7

N2 - Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is available through a one-pot Petasis 3-component reaction/Diels–Alder cascade reaction. We demonstrate the versatility of the approach through the synthesis of 35 exemplary compounds from the three classes, as well as by the production of 2188 final compounds, which have been included in the Joint European Compound Library of the European Lead Factory.

AB - Efficient access to diverse screening compounds with desirable, lead-like properties can be a bottleneck in early drug discovery and chemical biology. Herein we present an efficient, rapid route to three structurally distinct classes of compounds (A–C) from a single precursor, which in turn is available through a one-pot Petasis 3-component reaction/Diels–Alder cascade reaction. We demonstrate the versatility of the approach through the synthesis of 35 exemplary compounds from the three classes, as well as by the production of 2188 final compounds, which have been included in the Joint European Compound Library of the European Lead Factory.

KW - Cycloaddition

KW - Drug discovery

KW - Heterocycles

KW - Library synthesis

U2 - 10.1002/ejoc.201801551

DO - 10.1002/ejoc.201801551

M3 - Journal article

AN - SCOPUS:85058842528

SN - 1434-193X

VL - 2019

SP - 1061

EP - 1076

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 5

ER -

Generation of a Heteropolycyclic and sp3-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence

Abstract

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Citationsformater

Generation of a Heteropolycyclic and sp³-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence