Total Synthesis of Lyconesidine B, a <i>Lycopodium</i> Alkaloid with an Oxygenated, Amine-Type Fawcettimine Core
Tomohiro Kurose, Chihiro Tsukano, Takeshi Nanjo, Yoshiji Takemoto
Abstract
This report describes the total synthesis of the complex, oxygenated tetracyclic alkaloid, lyconesidine B. The key synthetic challenge involves diastereoselective generation of a decahydroquinoline ring with a quaternary carbon at the angular position via domino cyclopropanation, ring-opening, and reduction. Another crucial step is the domino ene-yne metathesis involving a quaternary ammonium ion, leading to the construction of a decahydroazaazulen framework.
Topics & Concepts
ChemistryQuaternary carbonTotal synthesisDominoMetathesisAmmoniumAmine gas treatingCyclopropanationRing (chemistry)StereochemistrySalt metathesis reactionCombinatorial chemistryOrganic chemistryEnantioselective synthesisCatalysisPolymerizationPolymerCholinesterase and Neurodegenerative DiseasesChemical synthesis and alkaloidsSynthetic Organic Chemistry Methods