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Total Synthesis of Notoryne
Sibadatta Senapati1, Shyamsundar Das1, Chepuri V Ramana1
1Division of Organic Chemistry , CSIR-National Chemical Laboratory , Dr. Homi Bhabha Road , Pune 411 008 , India.
The Journal of Organic Chemistry
|September 15, 2018
Summary
Researchers report the first total synthesis of notoryne, a complex molecule featuring a halogenated bifuranyl group and a cis-enyne. This achievement confirms its structure and configuration using a novel synthetic route.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Notoryne is a natural product with a unique structure containing a halogenated 2,2'-bifuranyl moiety and a cis-enyne unit.
- The total synthesis and structural confirmation of complex natural products are crucial for chemical biology and drug discovery.
Purpose of the Study:
- To achieve the first total synthesis of notoryne.
- To confirm the assigned relative and absolute configurations of notoryne.
Main Methods:
- Utilized a chiral pool intermediate derived from glucose diacetonide.
- Employed 5-endo bromo-etherification to construct the bis-furan core.
- Incorporated anomeric C-allylation and relay cross-metathesis for installing the cis-enyne unit.
Main Results:
- Successfully synthesized notoryne, validating the proposed synthetic strategy.
- Confirmed the relative and absolute configurations of the target molecule.
- Demonstrated the efficacy of the key synthetic transformations.
Conclusions:
- The first total synthesis of notoryne was accomplished.
- The synthetic route provides a reliable method for accessing notoryne and its analogs.
- This work advances the field of natural product synthesis and methodology development.
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