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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated
Myles W Smith1,2, Zhiyao Zhou3, Alison X Gao2
1Columbia University , Dept. of Chemistry, 3000 Broadway, New York, New York 10027, United States.
Abstract:
Herein is shown how a novel catalytic asymmetric propargylation of 3,4-dihydro-β-carboline, followed by a designed Au(I)/Ag(I)-mediated 6-endo-dig cyclization, can directly deliver the indolenine-fused methanoquinolizidine core of the akuammiline alkaloid strictamine in its native oxidation state, ultimately achieving a 7-step formal asymmetric total synthesis. Also demonstrated are how the cyclization products can rearrange into vincorine-type skeletons and a further use for the developed propargylation with the first catalytic asymmetric total synthesis of decarbomethoxydihydrogambirtannine.
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