Petasis/Diels-Alder/Cyclization Cascade Reactions for the Generation of Scaffolds with Multiple Stereogenic Centers and Orthogonal Handles for Library Production

Thomas Flagstad, Carlos M. G. Azevedo, Geanna Min, Anthony Willaume, Rémy Morgentin, Thomas E. Nielsen, Mads H. Clausen*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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Abstract

A new effective strategy for the synthesis of sp3‐rich small molecules for library production is presented. The key steps to generate complexity highlight Petasis 3‐component reaction followed by an intramolecular Diels‐Alder and cyclization to generate a densely enriched tricyclic or tetracyclic scaffolds with 3‐4 stereocenters with 3 handles for decoration. The strategy was used for the production of 143 molecules for the European Lead Factory.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number36
Pages (from-to)5023-5029
Number of pages8
ISSN1434-193X
DOIs
Publication statusPublished - 2018

Cite this

Flagstad, Thomas ; Azevedo, Carlos M. G. ; Min, Geanna ; Willaume, Anthony ; Morgentin, Rémy ; Nielsen, Thomas E. ; Clausen, Mads H. / Petasis/Diels-Alder/Cyclization Cascade Reactions for the Generation of Scaffolds with Multiple Stereogenic Centers and Orthogonal Handles for Library Production. In: European Journal of Organic Chemistry. 2018 ; Vol. 2018, No. 36. pp. 5023-5029.
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title = "Petasis/Diels-Alder/Cyclization Cascade Reactions for the Generation of Scaffolds with Multiple Stereogenic Centers and Orthogonal Handles for Library Production",
abstract = "A new effective strategy for the synthesis of sp3‐rich small molecules for library production is presented. The key steps to generate complexity highlight Petasis 3‐component reaction followed by an intramolecular Diels‐Alder and cyclization to generate a densely enriched tricyclic or tetracyclic scaffolds with 3‐4 stereocenters with 3 handles for decoration. The strategy was used for the production of 143 molecules for the European Lead Factory.",
author = "Thomas Flagstad and Azevedo, {Carlos M. G.} and Geanna Min and Anthony Willaume and R{\'e}my Morgentin and Nielsen, {Thomas E.} and Clausen, {Mads H.}",
year = "2018",
doi = "10.1002/ejoc.201800565",
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volume = "2018",
pages = "5023--5029",
journal = "European Journal of Organic Chemistry",
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Petasis/Diels-Alder/Cyclization Cascade Reactions for the Generation of Scaffolds with Multiple Stereogenic Centers and Orthogonal Handles for Library Production. / Flagstad, Thomas; Azevedo, Carlos M. G.; Min, Geanna; Willaume, Anthony; Morgentin, Rémy; Nielsen, Thomas E.; Clausen, Mads H.

In: European Journal of Organic Chemistry, Vol. 2018, No. 36, 2018, p. 5023-5029.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Petasis/Diels-Alder/Cyclization Cascade Reactions for the Generation of Scaffolds with Multiple Stereogenic Centers and Orthogonal Handles for Library Production

AU - Flagstad, Thomas

AU - Azevedo, Carlos M. G.

AU - Min, Geanna

AU - Willaume, Anthony

AU - Morgentin, Rémy

AU - Nielsen, Thomas E.

AU - Clausen, Mads H.

PY - 2018

Y1 - 2018

N2 - A new effective strategy for the synthesis of sp3‐rich small molecules for library production is presented. The key steps to generate complexity highlight Petasis 3‐component reaction followed by an intramolecular Diels‐Alder and cyclization to generate a densely enriched tricyclic or tetracyclic scaffolds with 3‐4 stereocenters with 3 handles for decoration. The strategy was used for the production of 143 molecules for the European Lead Factory.

AB - A new effective strategy for the synthesis of sp3‐rich small molecules for library production is presented. The key steps to generate complexity highlight Petasis 3‐component reaction followed by an intramolecular Diels‐Alder and cyclization to generate a densely enriched tricyclic or tetracyclic scaffolds with 3‐4 stereocenters with 3 handles for decoration. The strategy was used for the production of 143 molecules for the European Lead Factory.

U2 - 10.1002/ejoc.201800565

DO - 10.1002/ejoc.201800565

M3 - Journal article

VL - 2018

SP - 5023

EP - 5029

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 36

ER -