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A general synthetic route towards bastadins. Part 2: Synthesis of the western part of bastadins 4–16, and fully functionalized macrocycle of bastadin 12

✍ Scribed by Elias A. Couladouros; Vassilios I. Moutsos

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
215 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A general synthetic route for the construction of the western part of the macrocyclic bastadins 4-16 is presented. The western and the eastern segments were coupled using the imidazolide of the corresponding acid. The bromine at position y2 may be added at this advanced step regiospecifically, strengthening the convergence of the presented approach. Finally, the fully functionalized ~,to-aminoacid is cyclized with EDC affording the macrocyclic ring of bastadin-12 in 72% yield (3.5% overall yield).

📜 SIMILAR VOLUMES

A general synthetic route towards bastad
A general synthetic route towards bastadins. Part 1: Synthesis of the eastern part of bastadins 4–16
✍ Elias A. Couladouros; Vassilios I. Moutsos 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 276 KB

A general synthetic route for the construction of the eastern part of the macrocyclic bastadins 4-16 is presented. The brominated biaryl ethers are synthesized using the iodonium salt method. The synthesis is accomplished within 18 steps in 15.5% overall yield.