Skeletally Diverse Small Molecules Using a Build/Couple/Pair Strategy
نویسندگان
چکیده
Intermolecular couplings of simple building blocks using catalytic, stereoselective cross-Mannich reactions followed by intramolecular functional group-pairing reactions of easily accessed variants of the Mannich products are explored as a route to skeletally diverse small molecules. The synthetic pathway yields products having 12 different skeletons using only three steps and has the potential to enable substantial stereochemical diversification in the future.
منابع مشابه
Diversity-oriented synthesis of Lycopodium alkaloids inspired by the hidden functional group pairing pattern.
Natural products continue to provide a rich source of inspiration for both chemists and biologists. The efficient synthesis of bioactive natural products or natural product-like molecules has offered tremendous opportunities for complex biological processes exploration and drug discovery. However, because natural products usually contain numerous stereogenic centres and polycyclic ring systems,...
متن کاملGold(I)-Catalyzed Coupling Reactions for the Synthesis of Diverse Small Molecules Using the Build/Couple/Pair Strategy
The build/couple/pair strategy has yielded small molecules with stereochemical and skeletal diversity by using short reaction sequences. Subsequent screening has shown that these compounds can achieve biological tasks considered challenging if not impossible ('undruggable') for small molecules. We have developed gold(I)-catalyzed cascade reactions of easily prepared propargyl propiolates as a m...
متن کاملA programmable "build-couple" approach to the synthesis of heterofunctionalized polyvalent molecules.
A maximally divergent "build-couple" synthesis of heterofunctionalized polyvalent molecules is described. This strategic approach enables the synthesis of highly diverse polyvalent structures from a pre-programmed combinatorial set of modules.
متن کاملStereochemical and Skeletal Diversity Arising from Amino Propargylic Alcohols
An efficient synthetic pathway to the possible stereoisomers of skeletally diverse heterocyclic small molecules is presented. The change in shape brought about by different intramolecular cyclizations of diastereoisomeric amino propargylic alcohols is quantified using principal moment-of-inertia (PMI) shape analysis.
متن کاملDivergent Pd(II) and Au(III) mediated nitroalkynol cycloisomerizations.
A new cycloisomerization reaction comprising the simultaneous addition of nitro and alcohol groups across C≡C leading to skeletally diverse small molecules is documented.
متن کامل