A Formal Total Synthesis of (−)-FR901483, Using a Tandem Cationic Aza-Cope Rearrangement/Mannich Cyclization Approach
✍ Scribed by Brummond, Kay M.; Hong, Sang-phyo
- Book ID
- 118060148
- Publisher
- American Chemical Society
- Year
- 2005
- Tongue
- English
- Weight
- 374 KB
- Volume
- 70
- Category
- Article
- ISSN
- 0022-3263
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## Abstract The total synthesis of enantiomerically pure (−)‐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 25°C to give __cis__‐perhydroindolone **8** in 81% yield.
Key steps in this approach to umaryllidaceae alkaloids containing oxidation at the R-position of the pyrroline ring are (a) copper(H)-promoted rearrangement of aminocyclopentanol 11 to afford the 3-silylhydroindole 12, and (b) oxidation of 12 by the general procedures of Kumada and Fleming to give t