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 af dette arbejde

6 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	European Journal of Organic Chemistry
Vol/bind	2018
Udgave nummer	36
Sider (fra-til)	5023-5029
Antal sider	7
ISSN	1434-193X
DOI	https://doi.org/10.1002/ejoc.201800565
Status	Udgivet - 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

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.
I: European Journal of Organic Chemistry, Bind 2018, Nr. 36, 2018, s. 5023-5029.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › 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, bind 2018, nr. 36, s. 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.",

keywords = "Cascade reactions, Cycloaddition, Library synthesis, Petasis reaction, Synthetic methods",

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.}",

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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 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.

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

U2 - 10.1002/ejoc.201800565

DO - 10.1002/ejoc.201800565

M3 - Journal article

AN - SCOPUS:85054054090

SN - 1434-193X

VL - 2018

SP - 5023

EP - 5029

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

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