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

✍ Scribed by W. H. PEARSON; B. W. LIAN


Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis


Application of the 2-Azaallyl Anion Cycloaddition Method to an Enantioselective Total Synthesis of (+)-Coccinine. -The nonnatural enantiomer (XI) of the alkaloid (-)-coccinine is enantioselectively synthesized with cycloaddition of (VII) to (VIII) as the key step. -(PEARSON, W. H.;


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Application of the 2-Azaallyl Anion Cycl
✍ William H. Pearson; Brian W. Lian πŸ“‚ Article πŸ“… 1998 πŸ› John Wiley and Sons 🌐 English βš– 97 KB πŸ‘ 2 views

A highly functionalized perhydroindole is formed by the intramolecular [Ο€4s+Ο€2s] 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.