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

6 Citations (Scopus)

Abstract

A new effective strategy for the synthesis of sp³-rich small molecules for library production is presented. The key steps to generate complexity involve a Petasis three-component reaction followed by an intramolecular Diels–Alder and cyclization to generate a densely enriched tricyclic or tetracyclic scaffolds with 3–4 stereocenters and three 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	7
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201800565
Publication status	Published - 2018

Keywords

Cascade reactions
Cycloaddition
Library synthesis
Petasis reaction
Synthetic methods

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10.1002/ejoc.201800565

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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

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

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

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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 involve a Petasis three-component reaction followed by an intramolecular Diels–Alder and cyclization to generate a densely enriched tricyclic or tetracyclic scaffolds with 3–4 stereocenters and three handles for decoration. The strategy was used for the production of 143 molecules for the European Lead Factory.",

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AU - Azevedo, Carlos M.G.

AU - Min, Geanna

AU - Willaume, Anthony

AU - Morgentin, Rémy

AU - Nielsen, Thomas E.

AU - Clausen, Mads H.

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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 involve a Petasis three-component reaction followed by an intramolecular Diels–Alder and cyclization to generate a densely enriched tricyclic or tetracyclic scaffolds with 3–4 stereocenters and three handles for decoration. The strategy was used for the production of 143 molecules for the European Lead Factory.

KW - Cascade reactions

KW - Cycloaddition

KW - Library synthesis

KW - Petasis reaction

KW - Synthetic methods

UR - https://doi.org/10.1002/ejoc.201801730

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DO - 10.1002/ejoc.201800565

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SN - 1434-193X

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 36

ER -

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

Abstract

Keywords

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