Ontology highlight
ABSTRACT:
SUBMITTER: Pham HV
PROVIDER: S-EPMC3354770 | biostudies-literature | 2012
REPOSITORIES: biostudies-literature
Chemical science 20120202 3
Computational studies show that the base-mediated intramolecular Diels-Alder of tryptamine-derived Zincke aldehydes, used as a key step in the synthesis of the Strychnos alkaloids norfluorocurarine and strychnine, proceeds via a stepwise pathway. The experimentally determined importance of a potassium counterion in the base is explained by its ability to preorganize the Zincke aldehyde diene in an s-cis conformation suitable to bicyclization. Computation also supports the thermodynamic importanc ...[more]