ChemInform Abstract: Radical Cyclizations. A Convergent Total Synthesis of (.+-.)-γ-Lycorane.
✍ Scribed by Janine Cossy; Ludovic Tresnard; Domingo Gomez Pardo
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 33 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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Lycorane has been synthesized in ten steps from of (+)-γ-lycorane was achieved via an optically active unsaturated aldehyde intermediate. piperonylic alcohol. Two radical reactions were used successively to build the D and B rings. A formal synthesis [a] Laboratoire de Chimie Organique, associe ´au
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). -