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Radical Cyclizations – Synthesis of γ-Lycorane

✍ Scribed by Janine Cossy; Ludovic Tresnard; Domingo Gomez Pardo

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
331 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

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 CNRS, ESPCI, alcohol 7 (DEAD, PPh 3 , THF, 0 °C, 18 h) was not reactive 10, rue Vauquelin,

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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). -