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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Efficient syntheses of oncinotine and neooncinotine
Duen-Ren Hou1, Hsiu-Yi Cheng, Eng-Chi Wang
1Department of Chemistry, National Central University, Jung-Li City, Taoyuan, Taiwan 320, ROC.
Researchers synthesized natural alkaloids oncinotine and neooncinotine using efficient ring-closing metathesis. This study showcases a novel synthetic route for complex alkaloid structures.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Natural alkaloids like oncinotine and neooncinotine possess complex structures.
- Efficient synthetic methodologies are crucial for accessing such compounds.
Purpose of the Study:
- To synthesize oncinotine and neooncinotine.
- To explore the utility of ring-closing metathesis (RCM) in alkaloid synthesis.
Main Methods:
- Assembly of diene precursors from 2-allylpiperidine, 9-decenoic acid, and diamines.
- Utilized Michael addition and amidation reactions for precursor linkage.
- Employed Grubbs catalyst for ring-closing metathesis.
Main Results:
- Successful synthesis of oncinotine and neooncinotine.
- Formation of 17- and 18-membered lactams via RCM.
- Achieved yields of 50% and 68% for the respective lactams.
Conclusions:
- Ring-closing metathesis provides an efficient route to complex alkaloids.
- The developed synthetic strategy is effective for constructing oncinotine and neooncinotine.
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