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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
Author(s) -
Flagstad Thomas,
Azevedo Carlos M. G.,
Min Geanna,
Willaume Anthony,
Morgentin Rémy,
Nielsen Thomas E.,
Clausen Mads H.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800565
Subject(s) - stereocenter , chemistry , intramolecular force , cascade , combinatorial chemistry , component (thermodynamics) , stereochemistry , molecule , organic chemistry , catalysis , enantioselective synthesis , physics , chromatography , thermodynamics
A new effective strategy for the synthesis of sp 3 ‐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.