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ChemInform Abstract: Regio- and Enantioselective Prenyl Anion Transfer: Application to the Total Synthesis of (-)-Rosiridol.

โœ Scribed by B.-C. HONG; J.-H. HONG; Y.-C. TSAI

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

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Regio- and Enantioselective Prenyl Anion
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At elevated temperature (refluxing THF) prenyl anion adds regio- and enantioselectively to aldehyde 1 when a chiral, borneol-derived ligand is present. This reaction is the key stepin the first total synthesis of the monoterpene (-)-rosiridol (retrosynthesis is shown on the right). In addition, the

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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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