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

doi:10.1002/ejoc.201800565

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

Department of Chemistry

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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 language	English
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	36
Pages (from-to)	5023-5029
Number of pages	8
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201800565
Publication status	Published - 2018

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Flagstad, T., Azevedo, C. M. G., Min, G., Willaume, A., Morgentin, R., Nielsen, T. E., & Clausen, M. H. (2018). Petasis/Diels-Alder/Cyclization Cascade Reactions for the Generation of Scaffolds with Multiple Stereogenic Centers and Orthogonal Handles for Library Production. European Journal of Organic Chemistry, 2018(36), 5023-5029. https://doi.org/10.1002/ejoc.201800565

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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.",

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",

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volume = "2018",

pages = "5023--5029",

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Flagstad, T, Azevedo, CMG, Min, G, Willaume, A, Morgentin, R, Nielsen, TE & Clausen, MH 2018, 'Petasis/Diels-Alder/Cyclization Cascade Reactions for the Generation of Scaffolds with Multiple Stereogenic Centers and Orthogonal Handles for Library Production', European Journal of Organic Chemistry, vol. 2018, no. 36, pp. 5023-5029. https://doi.org/10.1002/ejoc.201800565

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

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

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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

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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.

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DO - 10.1002/ejoc.201800565

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JF - European Journal of Organic Chemistry

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ER -

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

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