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An efficient and selective synthesis of nakienone A involving a novel protocol for α-alkenylation of ketones via palladium-catalyzed alkenyl-alkenyl coupling

✍ Scribed by Milan Pour; Ei-ichi Negishi


Book ID
104256155
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
233 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


Nakienone A was synthesized for the first time from 3-methoxy-2-cyclopentenone, dienyl iodide 7, and LiCI-I2OMOM in 8 steps in 26% overall yield with full control of the alkene geometry using the Pal-catalyzed cross coupling reaction of a cyclopentenylzinc derivative 6a with 7 as a key step.


📜 SIMILAR VOLUMES


Highly selective synthesis of vitamin A
✍ Ei-ichi Negishi; Zbyslaw Owczarczyk 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 316 KB

Vitamin A has been synthesized cleanly and selectively with essentially complete control of stereoand regiochemistry in four linear and six overall steps from p-ionone and (E)-3-methyl-2-penten-4-yn-l-01 via Pd-catalyzed cross coupling of an alkenylzinc with an alkenyl iodide; the use of other metal