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Application of the 2-Azaallyl Anion Cycloaddition Method to an Enantioselective Total Synthesis of (+)-Coccinine

✍ Scribed by William H. Pearson; Brian W. Lian

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 97 KB
Volume: 37
Category: Article
ISSN: 0044-8249
DOI: 10.1002/(sici)1521-3773(19980703)37:12<1724::aid-anie1724>3.0.co;2-8

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✦ Synopsis

A highly functionalized perhydroindole is formed by the intramolecular [π4s+π2s] cycloaddition of a 2-azaallyl anion with a vinyl sulfide [Eq. (a)]. This is the key step in the total synthesis of (+)-coccinine, the enantiomer of the Amaryllidaceae alkaloid (-)-coccinine.

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