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Direct Alkenylation of Indoles with α‐Oxo Ketene Dithioacetals: Efficient Synthesis of Indole Alkaloids Meridianin Derivatives
Author(s) -
Yu Haifeng,
Yu Zhengkun
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900278
Subject(s) - ketene , trifluoroacetic acid , chemistry , indole test , guanidine , dichloromethane , condensation , organic chemistry , medicinal chemistry , physics , solvent , thermodynamics
Let's make 'meri' : Metal‐free direct alkenylation of indoles was realized by acid‐mediated substitution reactions of α‐oxo ketene dithioacetals with indoles in trifluoroacetic acid/dichloromethane, selectively affording β‐indolyl mono‐ and disubstituted α,β‐unsaturated carbonyl compounds (see scheme). Condensation of the indolyl/ketene monothioacetals and guanidine nitrate efficiently produced meridianin derivatives.