Ontology highlight
ABSTRACT:
SUBMITTER: Barcan GA
PROVIDER: S-EPMC3488149 | biostudies-literature | 2012 Nov
REPOSITORIES: biostudies-literature
Barcan Gregg A GA Patel Ashay A Houk K N KN Kwon Ohyun O
Organic letters 20121005 21
A highly torquoselective thermal triene 6π electrocyclization controls the relative stereochemistry between the C3 and C18 stereocenters of the dodecahydroindolo[2,3-a]benzo[g]quinolizine skeleton of reserpine-type alkaloids. Employing a tandem cross-coupling/electrocyclization protocol allowed us to form the requisite triene and ensure its subsequent cyclization. A novel low-temperature dibromoketene acetal Claisen rearrangement established the requisite exocyclic dienylbromide precursor for th ...[more]