Skeletally Diverse Small Molecules Using a Build/Couple/Pair Strategy
Open Access
- 10 March 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (7), 1559-1562
- https://doi.org/10.1021/ol900173t
Abstract
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.Keywords
This publication has 25 references indexed in Scilit:
- Towards the Optimal Screening Collection: A Synthesis StrategyAngewandte Chemie International Edition, 2007
- ChemBank: a small-molecule screening and cheminformatics resource databaseNucleic Acids Research, 2007
- An Oligomer-Based Approach to Skeletal Diversity in Small-Molecule SynthesisJournal of the American Chemical Society, 2006
- Experimental and Theoretical Studies on Stereo- and Regioselectivity in Intramolecular Nitrone−Alkene Cycloaddition of Hept-6-enoses Derived from CarbohydratesThe Journal of Organic Chemistry, 2006
- The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as NucleophilesThe Journal of Organic Chemistry, 2003
- Asymmetric Synthesis of Fused Bicyclic α-Amino Acids Having a Hexahydro-cyclopenta[c]pyridine Skeleton via Intramolecular Pauson−Khand Reaction of 1-Sulfonimidoyl-Substituted 5-Azaoct-1-en-7-ynesThe Journal of Organic Chemistry, 2003
- From Knowing to Controlling: A Path from Genomics to Drugs Using Small Molecule ProbesScience, 2003
- A Highly Enantioselective Route to Either Enantiomer of Both α- and β-Amino Acid DerivativesJournal of the American Chemical Society, 2002
- Mechanistic Considerations on the Oxime–Nitrone Isomerization and Intramolecular Cycloaddition Reaction of 3-(Alk-2-enylamino)propionaldehyde OximesBulletin of the Chemical Society of Japan, 2001
- An efficient asymmetric synthesis of 1.alpha.,25-(OH)2 vitamin D3 A-ring synthonThe Journal of Organic Chemistry, 1993