Generation of a Heteropolycyclic and sp3-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence
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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.; Min, Geanna K.; Macé, Yohan; Willaume, Anthony; Guilleux, Rachel; Velay, Mélanie; Bonnet, Karine; Morgentin, Remy; Nielsen, Thomas E.; Clausen, Mads H.
In: European Journal of Organic Chemistry, Vol. 2019, No. 5, 2019, p. 1061-1076.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Generation of a Heteropolycyclic and sp3-Rich Scaffold for Library Synthesis from a Highly Diastereoselective Petasis/Diels–Alder and ROM–RCM Reaction Sequence
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
Y1 - 2019
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
VL - 2019
SP - 1061
EP - 1076
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 5
ER -
ID: 212858083