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Synthesis applications of cationic aza-Cope rearrangements. 23. First total synthesis of amaryllidaceae alkaloids of the 5,11-methano morphanthridine type. An efficient total synthesis of (.+-.)-pancracine

โœ Scribed by Overman, Larry E.; Shim, Jaechul

Book ID
111961394
Publisher
American Chemical Society
Year
1991
Tongue
English
Weight
374 KB
Volume
56
Category
Article
ISSN
0022-3263

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Total Synthesis of (โˆ’)-Crinine. Use of T
Total Synthesis of (โˆ’)-Crinine. Use of Tandem Cationic Aza-Cope Rearrangement/Mannich Cyclizations for the Synthesis of Enantiomerically Pure Amaryllidaceae Alkaloids
โœ Larry E. Overman; Soji Sugai ๐Ÿ“‚ Article ๐Ÿ“… 1985 ๐Ÿ› John Wiley and Sons ๐ŸŒ German โš– 350 KB ๐Ÿ‘ 1 views

## Abstract The total synthesis of enantiomerically pure (โˆ’)โ€crinine (**1**) in 10 steps and 6% overall yield from cyclopentene oxide is reported. The key step was the rearrangement of **7** upon reaction with AgNO~3~ at 25ยฐC to give __cis__โ€perhydroindolone **8** in 81% yield.