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Cover Picture: Efficient Entry to the Hasubanan Alkaloids: First Enantioselective Total Syntheses of (−)‐Hasubanonine, (−)‐Runanine, (−)‐Delavayine, and (+)‐Periglaucine B (Angew. Chem. Int. Ed. 38/2011)
Author(s) -
Herzon Seth B.,
Calandra Nicholas A.,
King Sandra M.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105017
Subject(s) - enantioselective synthesis , cover (algebra) , stereochemistry , cyclopentadiene , total synthesis , adduct , chemistry , group (periodic table) , organic chemistry , catalysis , engineering , mechanical engineering
A unified synthetic strategy to prepare four hasubanan alkaloids, including hasubanonine (depicted), is described by S. B. Herzon et al. in their Communication on page 8863 ff. The synthesis features the application of 5‐trimethylsilylcyclopentadiene as a removable, stabilizing stereocontrol element. This controlling group serves to set the absolute configuration in the products and is thermally cleaved at approximately 80 °C lower than the parent cyclopentadiene adducts.