Two‐Step Catalytic Transformation ofN‐Benzyllactams to Alkaloids (±)‐Solenopsin, (±)‐Solenopsin A, and (+)‐Julifloridine

European Journal of Organic Chemistry
2020.0

Abstract

We report herein that the Ir and Cu-I bis-metal catalyzed reductive alkynylation of amides, a method that we developed previously, can be extended to 6-, 7-, and 8-membered lactams. The catalytic reductive alkynylation of 6-methyl-2-piperidinones and its 3-benzyloxy derivative proceeded with 2.3:1 to 7:1 2,6-trans/cis diastereoselectivities. The resulting piperidines were converted into alkaloids (+/-)-solenopsin, (+/-)-solenopsin A, and (+)-julifloridine all in only one step. This two-step approach to the alkaloids is much shorter and much efficient than the conventional multistep methods.

Knowledge Graph

Similar Paper

Two‐Step Catalytic Transformation ofN‐Benzyllactams to Alkaloids (±)‐Solenopsin, (±)‐Solenopsin A, and (+)‐Julifloridine
European Journal of Organic Chemistry 2020.0
Catalytic enantioselective reductive alkynylation of amides enables one-pot syntheses of pyrrolidine, piperidine and indolizidine alkaloids
Nature Communications 2023.0
A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine
Journal of the American Chemical Society 2021.0
Synthesis of (+)-solenopsin via Pd-catalyzed N-alkylation and cyclization
Bioscience, Biotechnology, and Biochemistry 2021.0
Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
Tetrahedron: Asymmetry 2013.0
Total Synthesis of Pyrrolidine and Piperidine Natural Products via TMSOTf-Mediated “5/6-endo-dig” Reductive Hydroamination of Enynyl Amines
Organic Letters 2023.0
Divergent Syntheses of Pyridoacridine Alkaloids via<scp>Palladium‐Catalyzed</scp> Reductive Cyclization with <scp>Nitro‐Biarenes</scp>
Chinese Journal of Chemistry 2021.0
Concise synthesis of bicyclic iminosugars via reductive functionalization of sugar-derived lactams and subsequent RCM reaction
Organic &amp; Biomolecular Chemistry 2021.0
The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16′‐epi‐Leucophyllidine
Angewandte Chemie International Edition 2021.0
Ir-Catalyzed Asymmetric Total Syntheses of Bisdehydrotuberostemonine D, Putative Bisdehydrotuberostemonine E and Structural Revision of the Latter
Journal of the American Chemical Society 2021.0