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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Total Synthesis of Macrocyclic Dysoxylactam A
D Prabhakar Reddy1,2, Biao Yu2,3
1Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, 1200 Cai Lun Road, Shanghai, 201203, China.
The total synthesis of dysoxylactam A, a novel macrolactam, was successfully achieved. This compound exhibits potent multi-drug-resistant reversing activities, offering new therapeutic possibilities.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
Background:
- Dysoxylactam A is a novel 17-membered macrolactam.
- It possesses potent multi-drug-resistant reversing activities.
Purpose of the Study:
- To achieve the total synthesis of dysoxylactam A.
- To explore its potential in overcoming drug resistance.
Main Methods:
- The synthesis started from 4-pentene-1-al.
- Key transformations included iterative aldol reactions and ring-closing metathesis.
- A longest linear sequence of 17 steps was employed.
Main Results:
- The total synthesis of dysoxylactam A was successfully completed.
- An overall yield of 9.5% was achieved.
- Stereochemically enriched polypropionate scaffold and macrocycle were constructed.
Conclusions:
- The total synthesis of dysoxylactam A is feasible.
- This synthesis provides a route to a compound with significant potential for reversing multi-drug resistance.
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