Total Synthesis of (-)-γ-Lycorane Using Diastereoselective 5-endotrig Radical Cyclization of N-Vinylic α-Halo Amides. -Radical cyclization of the acetamides (IV) proceeds with only moderate diastereoselectivity. Major product (Va) is converted to the title alkaloid (XI). -
✦ LIBER ✦
ChemInform Abstract: Effect of Temperature on 5-endo- and 4-exo-trig Radical Cyclizations of N-Vinylic α-Halo Amides.
✍ Scribed by H. ISHIBASHI; M. HIGUCHI; M. OHBA; M. IKEDA
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 34 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Effect of Temperature on 5-endo-and 4-exo-trig Radical Cyclizations of N-Vinylic α-Halo Amides.
-The reaction course is found to depend on the temperature. The method provides a new entry to tetrahydroindoles as versatile synthetic intermediates.
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