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Updated: Jan 21, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Synthesis of the Madangamine Alkaloid Core by a C-C Bond Activation Cascade
Matthew S Eastwood1, Christopher J Douglas1
1Department of Chemistry , University of Minnesota-Twin Cities , 207 Pleasant Street SE , Minneapolis , Minnesota 55455 , United States.
Abstract:
The diazatricyclic core of the madangamine alkaloids was synthesized from a densely functionalized cyclohexane derivative. An alkene and two cyanoformamide groups are used to form two new rings and a new quaternary stereocenter in a cascade reaction, which involves two Pd-catalyzed C-C bond activation steps. The synthesis of the cascade precursor involves an intramolecular Staudinger reaction of a vicinal diester that gives a [3.2.1]azabicyclooctane derivative, allowing the regioselective introduction of a monosubstituted alkene.
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