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Controlling Diastereoselectivity in the Tandem Microwave-Assisted Aza-Cope Rearrangement—Mannich Cyclization.

✍ Scribed by Benjamin F. Johnson; Edwin L. Marrero; Wesley A. Turley; Harriet A. Lindsay

Publisher
John Wiley and Sons
Year
2007
Weight
31 KB
Volume
38
Category
Article
ISSN
0931-7597

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✦ Synopsis

Abstract

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Total Synthesis of (−)-Crinine. Use of T
Total Synthesis of (−)-Crinine. Use of Tandem Cationic Aza-Cope Rearrangement/Mannich Cyclizations for the Synthesis of Enantiomerically Pure Amaryllidaceae Alkaloids
✍ Larry E. Overman; Soji Sugai 📂 Article 📅 1985 🏛 John Wiley and Sons 🌐 German ⚖ 350 KB 👁 1 views

## 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.